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  • 1. Abbasi, Alireza
    et al.
    Skripkin, Mikhail Yu.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Torapava, Natallia
    Ambidentate coordination of dimethyl sulfoxide in rhodium(III) complexes2011In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 40, no 5, p. 1111-1118Article in journal (Refereed)
    Abstract [en]

    The two dimethyl sulfoxide solvated rhodium(III) compounds, [Rh(dmso-kappa O)(5)(dmso-kappa S)](CF(3)SO(3))(3) (1 & 1* at 298 K and 100 K, respectively) and [Rh(dmso-kappa O)(3)(dmso-kappa S)(2)Cl](CF(3)SO(3))(2) (2), crystallize with orthorhombic unit cells in the space group Pna2(1) (No. 33), Z = 4. In the [Rh(dmso)(6)](3+) complex with slightly distorted octahedral coordination geometry, the Rh-O bond distance is significantly longer with O trans to S, 2.143(6) angstrom (1) and 2.100(6) angstrom (1*), than the mean Rh-O bond distance with O trans to O, 2.019 angstrom (1) and 2.043 angstrom (1*). In the [RhCl(dmso)(5)](3+) complex, the mean Rh-O bond distance with O trans to S, 2.083 angstrom, is slightly longer than that for O trans to Cl, 2.067(4) angstrom, which is consistent with the trans influence DMSO-kappa S > Cl > DMSO-kappa O of the opposite ligands. Raman and IR absorption spectra were recorded and analyzed and a complete assignment of the vibrational bands was achieved with support by force field calculations. An increase in the Rh-O stretching vibrational frequency corresponded to a decreasing trans-influence from the opposite ligand. The Rh-O force constants obtained were correlated with the Rh-O bond lengths, also including previously obtained values for other M(dmso)(6)(3+) complexes with trivalent metal ions. An almost linear correlation was obtained for the MO stretching force constants vs. the reciprocal square of the MO bond lengths. The results show that the metal ion-oxygen bonding of dimethyl sulfoxide ligands is electrostatically dominated in those complexes and that the stretching force constants provide a useful measure of the relative trans-influence of the opposite ligands in hexa-coordinated Rh(III)-complexes.

  • 2.
    Ahlford, Katrin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ekström, Jesper
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zaitsev, Alexey
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ryberg, Per
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Asymmetric transfer hydrogenation of ketones catalyzed by amino acid derived rhodium complexes: on the origin of enantioselectivity and enantioswitchability: Corrigendum to vol 15(2009) 42, pp. 11197-2010In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, no 35, p. 10610-10610Article in journal (Refereed)
  • 3.
    Ahlford, Katrin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ryberg, Per
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nordin, Mikael
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mechanistic investigation of enantioswitchable catalysts for asymmetric transfer hydrogenation2010In: Abstracts of Papers, 239th ACS National Meeting, San Francisco , CA, United States, March 21-25, 2010, Washington: American Chemical Society , 2010Conference paper (Other academic)
  • 4.
    Alam, Rauful
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Raducan, Mihai
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Diastereoselective allylboration of wide variety of carbonyl compounds using allylboronic acids: Construction of adjacent tertiary and quaternary centers2013In: Abstracts of papers of The American Chemical Society, American Chemical Society (ACS), 2013, Vol. 246, p. 364-ORGN-Conference paper (Refereed)
  • 5.
    Alam, Rauful
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vollgraff, Tobias
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of Adjacent Quaternary Stereocenters by Catalytic Asymmetric Allylboration2015In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 137, no 35, p. 11262-11265Article in journal (Refereed)
    Abstract [en]

    Allylboration of ketones with gamma-disubstituted allylboronic acids is performed in the presence of chiral BINOL derivatives. The reaction is suitable for single-step creation of adjacent quaternary stereocenters with high selectivity. We show that, with an appropriate choice of the chiral catalyst and the stereoisomeric prenyl substrate, full control of the stereo- and enantioselectivity is possible in the reaction.

  • 6. Barlind, Jonas G.
    et al.
    Buckett, Linda K.
    Crosby, Sharon G.
    Davidsson, Ojvind
    Emtenas, Hans
    Ertan, Anne
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Jurva, Ulrik
    Lemurell, Malin
    Gutierrez, Pablo Morentin
    Nilsson, Karolina
    O'Mahony, Gavin
    Petersson, Annika U.
    Redzic, Alma
    Wagberg, Fredrik
    Yuan, Zhong-Qing
    Identification and design of a novel series of MGAT2 inhibitors2013In: Bioorganic & Medicinal Chemistry Letters, ISSN 0960-894X, E-ISSN 1090-2120, Vol. 23, no 9, p. 2721-2726Article in journal (Refereed)
    Abstract [en]

    [Acyl CoA]monoacylglycerol acyltransferase 2 (MGAT2) is of interest as a target for therapeutic treatment of diabetes, obesity and other diseases which together constitute the metabolic syndrome. In this Letter we report our discovery and optimisation of a novel series of MGAT2 inhibitors. The development of the SAR of the series and a detailed discussion around some key parameters monitored and addressed during the lead generation phase will be given. The in vivo results from an oral lipid tolerance test (OLTT) using the MGAT2 inhibitor (S)-10, shows a significant reduction (68% inhibition relative to naive, p < 0.01) in plasma triacylglycerol (TAG) concentration.

  • 7.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Marcos, Rocio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sahoo, Suman
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Inge, A. Ken
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Zou, Xiaodong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    A Highly Active Bifunctional Iridium Complex with an Alcohol/Alkoxide-Tethered N-Heterocyclic Carbene for Alkylation of Amines with Alcohols2012In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 45, p. 14510-14519Article, review/survey (Refereed)
    Abstract [en]

    A series of new iridium(III) complexes containing bidentate N-heterocyclic carbenes (NHC) functionalized with an alcohol or ether group (NHC?OR, R=H, Me) were prepared. The complexes catalyzed the alkylation of anilines with alcohols as latent electrophiles. In particular, biscationic IrIII complexes of the type [Cp*(NHC-OH)Ir(MeCN)]2+2[BF4-] afforded higher-order amine products with very high efficiency; up to >99?% yield using a 1:1 ratio of reactants and 12.5 mol?% of Ir, in short reaction times (216 h) and under base-free conditions. Quantitative yields were also obtained at 50?degrees C, although longer reaction times (4860 h) were needed. A large variety of aromatic amines have been alkylated with primary and secondary alcohols. The reactivity of structurally related iridium(III) complexes was also compared to obtain insights into the mechanism and into the structure of possible catalytic intermediates. The IrIII complexes were stable towards oxygen and moisture, and were characterized by NMR, HRMS, single-crystal X-ray diffraction, and elemental analyses.

  • 8. Barzegar, Hamid Reza
    et al.
    Nitze, Florian
    Malolepszy, Artur
    Stobinski, Leszek
    Tai, Cheuk-Wai
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Wagberg, Thomas
    Water Assisted Growth of C-60 Rods and Tubes by Liquid-Liquid Interfacial Precipitation Method2012In: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 17, no 6, p. 6840-6853Article in journal (Refereed)
    Abstract [en]

    C-60 nanorods with hexagonal cross sections are grown using a static liquid-liquid interfacial precipitation method in a system of C-60/m-dichlorobenzene solution and ethanol. Adding water to the ethanol phase leads instead to C-60 tubes where both length and diameter of the C-60 tubes can be controlled by the water content in the ethanol. Based on our observations we find that the diameter of the rods/tubes strongly depends on the nucleation step. We propose a liquid-liquid interface growth model of C-60 rods and tubes based on the diffusion rate of the good C-60 containing solvent into the poor solvent as well as on the size of the crystal seeds formed at the interface between the two solvents. The grown rods and tubes exhibit a hexagonal solvate crystal structure with m-dichlorobenzene solvent molecules incorporated into the crystal structure, independent of the water content. An annealing step at 200 degrees C at a pressure <1 kPa transforms the grown structures into a solvent-free face centered cubic structure. Both the hexagonal and the face centered cubic structures are very stable and neither morphology nor structure shows any signs of degradation after three months of storage.

  • 9.
    Bogár, Krisztián
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Krumlinde, Patrik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bacsik, Zoltán
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Hedin, Niklas
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Bäckvall, Jan E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Heterogenized Wilkinson's Catalyst for Transfer Hydrogenation of Carbonyl Compounds2011In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 23, p. 4409-4414Article in journal (Refereed)
    Abstract [en]

    Wilkinson’s catalyst [RhCl(PPh3)3] was heterogenized on common silica by the use of a grafting/anchoring technique. The immobilized catalyst showed high activity and selectivity in transfer hydrogenation reactions of a range of carbonyl compounds in 2-propanol. Reactions carried out in 2-propanol at reflux afforded the corresponding alcohols in high yields in short reaction times. The heterogeneous feature ofthe catalyst allows for easy recovery and efficient reuse in the same reaction up to 5 times without any detectible loss of catalytic activity.

  • 10.
    Carson, Fabian
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Martínez-Castro, Elisa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Marcos, Rocio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    González Miera, Greco
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jansson, Kjell
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Zou, Xiaodong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Martin-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Effect of the functionalisation route on a Zr-MOF with an Ir-NHC complex for catalysis2015In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 51, no 54, p. 10864-10867Article in journal (Refereed)
    Abstract [en]

    A new iridium N-heterocyclic carbene (NHC) metallolinker has been synthesised and introduced into a metal-organic framework (MOF), for the first time, via two different routes: direct synthesis and postsynthetic exchange (PSE). The two materials were compared in terms of the Ir loading and distribution using X-ray energy dispersive spectroscopy (EDS), the local Ir structure using X-ray absorption spectroscopy (XAS) and the catalytic activity. The materials showed good activity and recyclability as catalysts for the isomerisation of an allylic alcohol.

  • 11. Cervin, Nicholas T.
    et al.
    Andersson, Linnea
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Ng, Jovice Boon Sing
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Olin, Pontus
    Bergström, Lennart
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Wågberg, Lars
    Lightweight and Strong Cellulose Materials Made from Aqueous Foams Stabilized by Nanofibrillated Cellulose2013In: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 14, no 2, p. 503-511Article in journal (Refereed)
    Abstract [en]

    A lightweight and strong porous cellulose material has been prepared by drying aqueous foams stabilized with surface-modified nanofibrillated cellulose (NFC). This material differs from other dry, particle stabilized foams in that renewable cellulose is used as stabilizing particles. Confocal microscopy and high speed video imaging show that the octylamine-coated, rod-shaped NFC nanoparticles residing at the air-liquid interface prevent the air bubbles from collapsing or coalescing. Stable wet foams can be achieved at solids content around 1% by weight. Careful removal of the water results in a cellulose-based material with a porosity of 98% and a density of 30 mg cm(-3). These porous cellulose materials have a higher Young's modulus than porous cellulose materials made from freeze-drying, at comparable densities, and have a compressive energy absorption of 56 kJ m(-3) at 80% strain. Measurement with the aid of an autoporosimeter revealed that most pores are in the range of 300 to 500 mu m.

  • 12.
    Deiana, Luca
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dziedzic, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ullah, Farman
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lin, Shuangzheng
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dynamic kinetic asymmetric transformation (DYKAT) by combination of amine and transition metal cascade catalysis2010In: Abstracts of Papers, 239th ACS National Meeting, San Francisco, CA, United States, March 21-25, 2010, Washington, D C: American Chemical Society , 2010Conference paper (Other academic)
  • 13.
    Deiana, Luca
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ghisu, Lorenza
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Afewerki, Samson
    Verho, Oscar
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Johnston, Eric V.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Hedin, Niklas
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Bacsik, Zoltan
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Mid-Sweden University, Sweden.
    Enantioselective Heterogeneous Synergistic Catalysis for Asymmetric Cascade Transformations2014In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 356, no 11-12, p. 2485-2492Article in journal (Refereed)
    Abstract [en]

    A modular design for a novel heterogeneous synergistic catalytic system, which simultaneously activates the electrophile and nucleophile by the combined activation modes of a separate metal and non-metal catalyst, for asymmetric cascade transformations on a solid surface is disclosed. This modular catalysis strategy generates carbocycles (up to 97.5: 2.5 er) as well as spirocyclic oxindoles (97.5: 2.5 to > 99: 0.5 er), containing all-carbon quaternary centers, in a highly enantioselective fashion via a one-pot dynamic relay process.

  • 14.
    Engström, Karin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Johnston, Eric V.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Verho, Oscar
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Gustafson, Karl P. J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Shakeri, Mozaffar
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tai, Cheuk-Wai
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Co-immobilization of an Enzyme and a Metal into the Compartments of Mesoporous Silica for Cooperative Tandem Catalysis: An Artificial Metalloenzyme2013In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, no 52, p. 14006-14010Article in journal (Refereed)
    Abstract [en]

    Surpassing nature: A hybrid catalyst in which Candida antarctica lipase B and a nanopalladium species are co-immobilized into the compartments of mesoporous silica is presented. The metal nanoparticles and the enzyme are in close proximity to one another in the cavities of the support. The catalyst mimics a metalloenzyme and was used for dynamic kinetic resolution of a primary amine in high yield and excellent enantioselectivity.

  • 15.
    Eriksson, Lars
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Methyl 3-O-α-l-fucopyranosyl β-d-glucopyranoside tetrahydrate2012In: Acta Crystallographica Section E: Structure Reports Online, ISSN 1600-5368, E-ISSN 1600-5368, Vol. 68, p. o3180-o3181Article in journal (Refereed)
    Abstract [en]

    The title compound, C13H24O10·4H2O, is the methyl glycoside of a disaccharide structural element present in the backbone of the capsular polysaccharide from Klebsiella K1, which contains only three sugars and a substituent in the polysaccharide repeating unit. The conformation of the title disaccharide is described by the glycosidic torsion angles ϕH = 51.1 (1)° and ψH = 25.8 (1)°. In the crystal, a number of O—HO hydrogen bonds link the methyl glycoside and water mol­ecules, forming a three-dimensional network. One water mol­ecule is disordered over two positions with occupancies of 0.748 (4) and 0.252 (4).

  • 16.
    Frigell, Jens
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Cumpstey, Ian
    Carbasugar analogues of galactofuranosides: β-O-linked derivativesManuscript (preprint) (Other academic)
    Abstract [en]

    A selectively protected carbasugar analogue of β-galactofuranose was synthesised from glucose using ring-closing metathesis as the key step. The carbasugar was converted into an α-galacto configured 1,2-epoxide, which was an effective electrophile in Lewis acid catalysed coupling reactions with alcohols. The epoxide was opened with regioselective attack at C-1 to give β-galacto configured C-1 ethers. Using carbohydrates as nucleophiles, we synthesised a number of pseudodisaccharides.

  • 17.
    Gustafson, Karl P. J.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Guðmundsson, Arnar
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bajnóczi, Éva
    Ning, Yuan
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Persson, Ingmar
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    In-Situ Structure Determination of a Ruthenium Racemization Catalyst and its Activated Intermediates using X-ray Absorption SpectroscopyManuscript (preprint) (Other academic)
  • 18.
    Gustafson, Karl P. J.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Görbe, Tamás
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    de Gonzalo Calvo, Gonzalo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Yuan, Ning
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Schreiber, Cynthia
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Shchukarev, Andrey
    Tai, Cheuk-Wai
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Persson, Ingmar
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Application and further structure elucidation of Pd(0)-CalB CLEA biohybrid catalyst- Chemoenzymatic dynamic kinetic resolution of primary benzylic aminesManuscript (preprint) (Other academic)
  • 19.
    Görbe, Tamás
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Gustafson, Karl P. J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Verho, Oscar
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kervefors, Gabriella
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zheng, Haoquan
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Zou, Xiaodong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Johnston, Eric V.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Design of a Pd(0)-CalB CLEA Biohybrid Catalyst and Its Application in a One-Pot Cascade Reaction2017In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 7, no 3, p. 1601-1605Article in journal (Refereed)
    Abstract [en]

    Herein, a design of a biohybrid catalyst is described, consisting of Pd nanoparticles and a cross-linked network of aggregated lipase B enzyme of Candida antarctica (CalB CLEA) functioning as an active support for the Pd nanoparticles. Both entities of the hybrid catalyst showed good catalytic activity. The applicability was demonstrated in a one-pot reaction, where the Pd-catalyzed cycloisomerization of 4-pentynoic acid afforded a lactone that serves as an acyl donor in a subsequent selective enzymatic kinetic resolution of a set of sec-alcohols. The catalyst proved to be robust and could be recycled five times without a significant loss of activity.

  • 20.
    Hamark, Christoffer
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Landström, Jens
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ethyl 3,6-di-O-benzyl-2-deoxy-N-phthalimido-1-thio-β-D-glucopyranoside2010In: Acta Crystallographica Section E: Structure Reports Online, ISSN 1600-5368, E-ISSN 1600-5368, Vol. E66, p. o3250-o3251Article in journal (Refereed)
    Abstract [en]

    In the title compound, C30H31NO6S, the plane of the N-phthalimido group is nearly orthogonal to the least-squares plane of the sugar ring (defined by atoms C2, C3, C5 and O5 using standard glucose nomenclature), making a dihedral angle of 72.8 (1)°. The thioethyl group has the exo-anomeric conformation. The hydroxy group forms an intermolecular hydrogen bond to the O atom in the sugar ring, generating [100] chains. There are four close - contacts with centroid-centroid distances less than 4.0 Å, all with dihedral angles between the interacting systems of only 8°, supporting energetically favourable stacking interactions

  • 21.
    Hamark, Christoffer
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Landström, Jens
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ethyl 4,6-O-benzylidene-2-deoxy-N-phthalimido-1-thio-β-D-glucopyranoside2010In: Acta Crystallographica Section E: Structure Reports Online, ISSN 1600-5368, E-ISSN 1600-5368, Vol. E66, p. o3249-Article in journal (Refereed)
  • 22.
    Johnston, Eric V.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Verho, Oscar
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kärkäs, Markus
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Shakeri, Mozaffar
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tai, Cheuk-Wai
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Palmgren, Pål
    Eriksson, Kristofer
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Oscarsson, Sven
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Highly dispersed palladium nanoparticles on mesocellular foam: an efficient and recyclable heterogeneous catalyst for alcohol oxidation2012In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 39, p. 12202-12206Article in journal (Refereed)
  • 23. Karlsson, Erik A.
    et al.
    Lee, Bao-Lin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Liao, Rong-Zhen
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Åkermark, Torbjörn
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Kärkäs, Markus D.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Becerril, Valeria Saavedra
    Abrahamsson, Maria
    Siegbahn, Per E. M.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zou, Xiaodong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis and electron transfer processes in a new family of coupled Mn2–Ru complexesManuscript (preprint) (Other academic)
  • 24.
    Karlsson, Erik A.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lee, Bao-Lin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Åkermark, Torbjörn
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Johnston, Eric V.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kärkäs, Markus D.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Hansson, Örjan
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Photosensitized water oxidation by use of a bioinspired manganese catalyst2011In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, no 49, p. 11715-11718Article in journal (Refereed)
  • 25. Kotsyubynskyy, Dmytro
    et al.
    Zerbetto, Mirco
    Šoltésová, Mária
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK). Charles University Prague .
    Engström, Olof
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Pendrill, Robert
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kowalewski, Josef
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Polimeno, Antonin
    Stochastic Modeling of Flexible Biomolecules Applied to NMR Relaxation: 2. Interpretation of Complex Dynamics in Linear Oligosaccharides2012In: Journal of Physical Chemistry B, ISSN 1520-6106, E-ISSN 1520-5207, Vol. 116, no 50, p. 14541-14555Article in journal (Refereed)
    Abstract [en]

    A computational stochastic approach is applied to the description of flexible molecules. By combining (i) molecular dynamics simulations, (ii) hydrodynamics approaches, and (iii) a multidimensional diffusive description for internal and global dynamics, it is possible to build an efficient integrated approach to the interpretation of relaxation processes in flexible systems. In particular, the model is applied to the interpretation of nuclear magnetic relaxation measurements of linear oligosaccharides, namely a mannose-containing trisaccharide and the pentasaccharide LNF-1. Experimental data are reproduced with sufficient accuracy without free model parameters.

  • 26.
    Kärkäs, Markus D.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Laine, Tanja M.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Åkermark, Torbjörn
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Molecular Single-site Ruthenium Complexes Containing a Basic Site: The Use of Structure-activity RelationshipsManuscript (preprint) (Other academic)
    Abstract [en]

    A series of single-site ruthenium(III) complexes (2a-d) were synthesized and characterized, and employed in the oxidation of H2O. A linear free-energy relationship study was conducted in order to establish a correlation between the electrochemical properties and the electronic parameters of the introduced substituents in complexes 2a-d.

  • 27.
    Kärkäs, Markus D.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Åkermark, Torbjörn
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Chen, Hong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK). China University of Geosciences .
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    A Tailor-Made Molecular Ruthenium Catalyst for the Oxidation of Water and Its Deactivation through Poisoning by Carbon Monoxide2013In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, no 15, p. 4189-4193Article in journal (Refereed)
  • 28.
    Lee, Bao-Lin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Karlsson, Erik A.
    Kärkäs, Markus D.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Åkermark, Torbjörn
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Johnston, Eric
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Das, Biswanath
    Nordlander, Ebbe
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Light-induced water oxidation by a dinuclear iron-based molecular catalystManuscript (preprint) (Other academic)
  • 29.
    Lee, Bao-Lin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kärkäs, Markus D.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Johnston, Eric V.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Inge, Andrew K.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Tran, Lien-Hoa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Xu, Yunhua
    Hansson, Örjan
    Zou, Xiaodong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis and characterization of oligonuclear Ru, Co, and Cu oxidation catalysts2010In: European Journal of Inorganic Chemistry, ISSN 1434-1948, E-ISSN 1099-1948, no 34, p. 5462-5470Article in journal (Refereed)
    Abstract [en]

    In this work, we report the preparation and crystal structures of three new oligonuclear complexes, Ru-2(bbpmp)(mu-OAc)(3) (4), [Co-2(bbpmp)(mu-OAc)(mu-OMe)](PF6) (5), [Cu-4(Hbbpmp)(2)(mu-OAc)(H2O)(2)](OAc)(PF6)(2) (6) {H(3)bbpmp = 2,6-bis[(2-hydroxybenzyl)-(2-pyridylmethyl)aminomethyl]-4-methylphenol (3)}. The structures of the complexes were determined by single-crystal X-ray diffraction. The oxidation states of ruthenium, cobalt and copper in the complexes are +3, +3 and +2, respectively. In 4 and 5, Ru-III and Co-III are coordinated to four oxygen and two nitrogen atoms in an octahedral geometry, while in 6, Cu-II adopts both octahedral (CuN2O4) and square-pyramidal (CuN2O3) geometry. The potential of the three complexes as oxidation catalysts has been investigated.

  • 30.
    Lin, Shuangzheng
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Deiana, Luca
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Zhang, Qiong
    Leijonmarck, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dynamic kinetic asymmetric domino oxa-Michael/carbocyclization by combination of transition-metal and amine catalysis: catalytic enantioselective synthesis of dihydrofurans2010In: Chemistry - A European Journal, ISSN 0947-6538, Vol. 16, no 47, p. 13930-13934Article in journal (Refereed)
  • 31.
    Liu, Leifeng
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Yu, Zheng-Bao
    Chen, Hong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK). China University of Geosciences, People's Republic of China .
    Deng, Youqian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lee, Bao-Lin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK). Peking University, People's Republic of China .
    Disorder in Extra-Large Pore Zeolite ITQ-33 Revealed by Single Crystal XRD2013In: Crystal Growth & Design, ISSN 1528-7483, E-ISSN 1528-7505, Vol. 13, no 10, p. 4168-4171Article in journal (Refereed)
    Abstract [en]

    The single crystal of the extra-large pore zeolite, ITQ-33, was obtained and used to explore its crystal structure details. The ITQ-33 structure was found to be disordered with the columnar periodic building unit, explaining the morphology changes upon the different Si/Ge ratio, and the formation of the hierarchical structure from assembling of ITQ-33 nanofibers.

  • 32. Ma, Guangning
    et al.
    Lin, Shuangzheng
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ibrahem, Ismail
    Kubik, Grzegorz
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Liu, Leifeng
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Cordova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Achiral Co-Catalyst Induced Switches in Catalytic Asymmetric Reactions on Racemic Mixtures (RRM): From Stereodivergent RRM to Stereoconvergent Deracemization by Combination of Hydrogen Bond Donating and Chiral Amine Catalysts2012In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 354, no 14-15, p. 2865-2872Article in journal (Refereed)
    Abstract [en]

    A stereochemical divergent approach for the highly enantioselective synthesis of distinct bicyclic products with multiple stereocenters from a racemate using a single chiral catalyst is disclosed. It is based on switches of the overall reaction pathways in the chiral amine-catalyzed cascade reactions between racemic ?-nitro ketones and a,beta-unsaturated aldehydes using different achiral co-catalysts. The utility of the method is exemplified by the highly diasteroselective switch and stereoconvergent deracemization process by combination of chiral amine and achiral hydrogen-bond-donating catalysts.

  • 33.
    Malmgren, Joel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nagendiran, Anuja
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tai, Cheuk-Wai
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    C-2 Selective Arylation of Indoles with Heterogeneous Nanopalladium and Diaryliodonium Salts2014In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, no 42, p. 13531-13535Article in journal (Refereed)
    Abstract [en]

    A simple and efficient method to prepare synthetically useful 2-arylindoles is presented, using a heterogeneous Pd catalyst and diaryliodonium salts in water under mild conditions. A remarkably low leaching of metal catalyst was observed under the applied conditions. The developed protocol is highly C-2 selective and tolerates structural variations both in the indole and in the diaryliodonium salt. Arylations of both NH indoles and N-protected indoles with ortho-substituted, electron-rich, electron-deficient, or halogenated diaryliodonium salts were achieved to give the desired products in high to excellent isolated yields within 6 to 15 h at room temperature or 40 °C.

  • 34.
    Nagendiran, Anuja
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Pascanu, Vlad
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bermejo Gómez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    González Miera, Greco
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tai, Cheuk-Wai
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Verho, Oscar
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mild and Selective Catalytic Hydrogenation of the C=C Bond in a,b-Unsaturated Carbonyl Compounds Using Supported Palladium Nanoparticles2016In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 22, no 21, p. 7184-7189Article in journal (Refereed)
    Abstract [en]

    Chemoselective reduction of the C=C bond in a variety of α,β-unsaturated carbonyl compounds using supported palladium nanoparticles is reported. Three different heterogeneous catalysts were compared using 1 atm of H2: 1) nano-Pd on a metal–organic framework (MOF: Pd0-MIL-101-NH2(Cr)), 2) nano-Pd on a siliceous mesocellular foam (MCF: Pd0-AmP-MCF), and 3) commercially available palladium on carbon (Pd/C). Initial studies showed that the Pd@MOF and Pd@MCF nanocatalysts were superior in activity and selectivity compared to commercial Pd/C. Both Pd0-MIL-101-NH2(Cr) and Pd0-AmP-MCF were capable of delivering the desired products in very short reaction times (10–90 min) with low loadings of Pd (0.5–1 mol %). Additionally, the two catalytic systems exhibited high recyclability and very low levels of metal leaching.

  • 35.
    Pascanu, Vlad
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Carson, Fabian
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Vico Solano, Marta
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Su, Jie
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Zou, Xiaodong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Johansson, Magnus J.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Selective Heterogeneous C−H Activation/Halogenation Reactions Catalyzed by Pd@MOF Nanocomposites2016In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 22, no 11, p. 3729-3737Article in journal (Refereed)
    Abstract [en]

    A directed heterogeneous C−H activation/halogenation reaction catalyzed by readily synthesized Pd@MOF nanocatalysts was developed. The heterogeneous Pd catalysts used were a novel and environmentally benign Fe-based metal–organic framework (MOF) (Pd@MIL-88B-NH2(Fe)) and the previously developed Pd@MIL-101-NH2(Cr). Very high conversions and selectivities were achieved under very mild reaction conditions and in short reaction times. A wide variety of directing groups, halogen sources, and substitution patterns were well tolerated, and valuable polyhalogenated compounds were synthesized in a controlled manner. The synthesis of the Pd-functionalized Fe-based MOF and the recyclability of the two catalysts are also presented.

  • 36.
    Pathipati, Stalin R.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    van der Werf, Angela
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Selander, Nicklas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Diastereoselective Synthesis of Cyclopenta[c]furans by a Catalytic Multicomponent Reaction2016In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, no 39, p. 11863-11866Article in journal (Refereed)
    Abstract [en]

    A diastereoselective three-component reaction between alkynyl enones, aldehydes and secondary amines is reported. With the aid of a benign indium catalyst, a range of highly substituted cyclopenta[c]furan derivatives can be obtained in a single-step procedure. The formation of the stereodefined heterocyclic motifs takes place via in situ generation of enamines followed by two sequential cyclization steps.

  • 37.
    Rabten, Wangchuk
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kärkäs, Markus D.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Åkermark, Torbjörn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Chen, Hong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Liao, Rong-Zhen
    Tinnis, Fredrik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Siegbahn, Per E. M.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Andersson, Pher G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Catalytic Water Oxidation by a Molecular Ruthenium Complex: Unexpected Generation of a Single-Site Water Oxidation Catalyst2015In: Inorganic Chemistry, ISSN 0020-1669, E-ISSN 1520-510X, Vol. 54, no 10, p. 4611-4620Article in journal (Refereed)
    Abstract [en]

    The increasing energy demand calls for the development of sustainable energy conversion processes. Here, the splitting of H2O to O-2 and H-2, or related fuels, constitutes an excellent example of solar-to-fuel conversion schemes. The critical component in such schemes has proven to be the catalyst responsible for mediating the four-electron oxidation of H2O to O-2. Herein, we report on the unexpected formation of a single-site Ru complex from a ligand envisioned to accommodate two metal centers. Surprising N-N bond cleavage of the designed dinuclear ligand during metal complexation resulted in a single-site Ru complex carrying a carboxylate amide motif. This ligand lowered the redox potential of the Ru complex sufficiently to permit H2O oxidation to be carried out by the mild one-electron oxidant [Ru(bpy)(3)](3+) (bpy = 2,2'-bipyridine). The work thus highlights that strongly electron-donating ligands are important elements in the design of novel, efficient H2O :oxidation catalysts.

  • 38.
    Rabten, Wangchuk
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Åkermark, Torbjörn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kärkäs, Markus D.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Chen, Hong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK). China University of Geosciences, China.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK). Peking University, China.
    Andersson, Pher G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    A ruthenium water oxidation catalyst based on a carboxamide ligand2016In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 45, no 8, p. 3272-3276Article in journal (Refereed)
    Abstract [en]

    Herein is presented a single-site Ru complex bearing a carboxamide-based ligand that efficiently manages to carry out the fourelectron oxidation of H2O. The incorporation of the negatively charged ligand framework significantly lowered the redox potentials of the Ru complex, allowing H2O oxidation to be driven by the mild oxidant [Ru(bpy)(3)](3+). This work highlights that the inclusion of amide moieties into metal complexes thus offers access to highly active H2O oxidation catalysts.

  • 39.
    Rios, Ramón
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Schyman, Patric
    Sundén, Henrik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ullah, Farman
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Chen, Li-Jun
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Laaksonen, Aatto
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nonlinear effects in asymmetric amino acid catalysis by multiple interconnected stereoselective catalytic networks2010In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, no 47, p. 13935-13940Article in journal (Refereed)
  • 40.
    Shakeri, Mozaffar
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tai, Cheuk-Wai
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Göthelid, Emmanuelle
    Oscarsson, Sven
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Small Pd Nanoparticles Supported in Large Pores of Mesocellular Foam: An Excellent Catalyst for Racemization of Amines2011In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 17, no 47, p. 13269-13273Article in journal (Refereed)
    Abstract [en]

    Highly dispersed palladium nanoparticles (1–2 nm) supported in large-pore mesocellular foam (MCF; 29 nm) were synthesized. The Pd-nanocatalyst/MCF system was characterized by transmission electron microscopy (TEM), powder X-ray diffraction (XRD) and X-ray photoelectron spectroscopy (XPS). The performance of the Pd nanocatalyst obtained was examined for amine racemization. The Pd nanocatalyst showed higher activity and selectivity toward racemization of (S)-1-phenylethyl amine than any other amine racemization catalyst reported so far and it could be reused several times. Our data from TEM and XRD suggest a restructuring of the Pd nanocatalyst from amorphous to crystalline and an increase in Pd nanocatalyst size during the racemization reaction. This led to an unexpected increase of activity after the first use. The Pd nanocatalyst obtained can be integrated with other resolving processes of racemic organic compounds to increase the yield of chiral organic products.

  • 41.
    Shatskiy, Andrey
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lomoth, Reiner
    Abdel-Magied, Ahmed F.
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Nuclear Materials Authority, Egypt.
    Rabten, Wangchuk
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Laine, Tanja M.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Chen, Hong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK). KTH Royal Institute of Technology, Sweden.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Andersson, Pher G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kärkäs, Markus D.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Johnston, Eric V.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Catalyst-solvent interactions in a dinuclear Ru-based water oxidation catalyst2016In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 45, no 47, p. 19024-19033Article in journal (Refereed)
    Abstract [en]

    Photocatalytic water oxidation represents a key process in conversion of solar energy into fuels and can be facilitated by the use of molecular transition metal-based catalysts. A novel straightforward approach for covalent linking of the catalytic units to other moieties is demonstrated by preparation of a dinuclear complex containing two [Ru(pdc)(pic)(3)]-derived units (pdc = 2,6-pyridinedicarboxylate, pic = 4-picoline). The activity of this complex towards chemical and photochemical oxidation of water was evaluated and a detailed insight is given into the interactions between the catalyst and acetonitrile, a common co-solvent employed to increase solubility of water oxidation catalysts. The solvent-induced transformations were studied by electrochemical and spectroscopic techniques and the relevant quantitative parameters were extracted.

  • 42.
    Stridfeldt, Elin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Seemann, Alexandra
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bouma, Marinus J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dey, Chandan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ertan, Anne
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis, Characterization and Unusual Reactivity of Vinylbenziodoxolones-Novel Hypervalent Iodine Reagents2016In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 22, no 45, p. 16066-16070Article in journal (Refereed)
    Abstract [en]

    A novel type of hypervalent iodine(III) reagents, vinylbenziodoxolones (VBX), has been synthesized in a one-pot reaction from 2-iodobenzoic acid. VBX is bench stable, has been thoroughly characterized and the cyclic structure is supported by X-ray analysis. The reactivity of VBX was investigated in vinylation of nitrocyclohexane, and delivered vinylated products with opposite regioselectivity compared to acyclic vinyl(aryl) iodonium salts. The reagents could become a powerful tool in vinylation reactions under both metal-free and metal-catalyzed conditions.

  • 43.
    Sundström, Maria
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Radiosynthesis of Perfluoroalkyl Substances: Chemical analysis, uptake, distribution, and partitioning studies2012Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Perfluoroalkyl substances (PFASs) are widely utilized manmade chemicals. Their properties have made them highly appreciated in a variety of industrial and consumer product applications, including fire-fighting foams, hydraulic fluids, as well as in cookware and food contact papers.

    However, some of the PFASs are highly persistent in the environment and their toxicological profiles are of concern. Voluntary and regulatory efforts have been taken to reduce the environmental levels of PFASs. These actions have resulted in a reduction of PFASs in human milk from Stockholm as presented in this thesis.

    The radiosyntheses of 35S-PFOS, 35S-PFBS, and 14C-PFOA presented herein were applied for distribution studies in mice but also for solubility and adhesion experiments of common laboratory solvents and buffers. The radiosynthesis employed reactive Grignard reagents, perfluoroalkyliodides, and 35S-sulfur dioxide or 14C-carbon dioxide. The distribution studies were performed with 35S-PFOS on both pregnant mice and their offspring as well as on male mice. The mice were subjected to whole-body autoradiography and the tissues were analyzed by liquid scintillation counting. Liver and lungs were the target organs for 35S-PFOS in the dams. The fetuses and pups had remarkable high levels of 35S-PFOS in their lungs as well as in the brain. The male mice were given a high dose and a more environmental relevant dose of 35S-PFOS. PFOS was transferred from the blood to the tissues as the dose increased.

    In another study the distribution pattern of the shorter homologue PFBS was compared to PFOS. 35S-PFBS was utilized and demonstrated a 5-40 fold lower tissue levels in comparison to PFOS.

    The pharmacokinetic parameters determined for PFHxS in mice, rats, and monkeys will provide valuable insight in establishing a proper risk assessment for this compound. The study confirms the common species differences in serum elimination half-life that are associated with PFASs.

  • 44. Svensson, Anna
    et al.
    Larsson, Per Tomas
    Salazar-Alvarez, German
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Wagberg, Lars
    Preparation of dry ultra-porous cellulosic fibres: Characterization and possible initial uses2013In: Carbohydrate Polymers, ISSN 0144-8617, E-ISSN 1879-1344, Vol. 92, no 1, p. 775-783Article in journal (Refereed)
    Abstract [en]

    Dry ultra-porous cellulose fibres were obtained using a liquid exchange procedure in which water was replaced in the following order: water, methanol, acetone, and finally pentane: thereafter, the fibres were dried with Ar(g). The dry samples (of TEMPO-oxidized dissolving pulp) had a specific surface area of 130 m(2) g(-1) as measured using BET nitrogen gas adsorption. The open structure in the dry state was also revealed using field emission scanning electron microscopy. This dry open structure was used as a scaffold for in situ polymerization. Both poly(methyl methacrylate) and poly(butylacrylate) were successfully used as matrix polymers for the composite material (fibre/polymer), comprising approximately 20 wt% fibres. Atomic force microscopy phase imaging indicated a nanoscale mixing of the matrix polymer and the cellulose fibril aggregates and this was also supported by mechanical testing of the prepared composite where the open fibre structure produced superior composites. The fibre/polymer composite had a significantly reduced water absorption capacity also indicating an efficient filling of the fibre structure with the matrix polymer.

  • 45.
    Tinnis, Fredrik
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Verho, Oscar
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Gustafson, Karl P. J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tai, Cheuk-Wai
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Efficient Palladium-Catalyzed Aminocarbonylation of Aryl Iodides Using Palladium Nanoparticles Dispersed on Siliceous Mesocellular Foam2014In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, no 20, p. 5885-5889Article in journal (Refereed)
    Abstract [en]

    A highly dispersed nanopalladium catalyst supported on mesocellular foam (MCF), was successfully used in the heterogeneous catalysis of aminocarbonylation reactions. During the preliminary evaluation of this catalyst it was discovered that the supported palladium nanoparticles exhibited a “release and catch” effect, meaning that a minor amount of the heterogeneous palladium became soluble and catalyzed the reaction, after which it re-deposited onto the support.

  • 46.
    Verho, Oscar
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dilenstam, Marléne D. V.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kärkäs, Markus
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Johnston, Eric
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Åkermark, Torbjörn
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Application and mechanistic studies of a water-oxidation catalyst in alcohol oxidation by employing oxygen-transfer reagents2012In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 52, p. 16947-16954Article in journal (Refereed)
    Abstract [en]

    By using a dimeric ruthenium complex in combination with tert-butyl hydrogen peroxide (TBHP) as stoichiometric oxidant, a mild and efficient protocol for the oxidation of secondary benzylic alcohols was obtained, thereby giving the corresponding ketones in high yields within 4 h. However, in the oxidation of aliphatic alcohols, the TBHP protocol suffered from low conversions owing to a competing Ru-catalyzed disproportionation of the oxidant. Gratifyingly, by switching to Oxone (2 KHSO5KHSO4K2SO4 triple salt) as stoichiometric oxidant, a more efficient and robust system was obtained that allowed for the oxidation of a wide range of aliphatic and benzylic secondary alcohols, giving the corresponding ketones in excellent yields. The mechanism for these reactions is believed to involve a high-valent RuV–oxo species. We provide support for such an intermediate by means of mechanistic studies.

  • 47.
    Verho, Oscar
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Gao, Feifei
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Johnston, Eric V.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Wan, Wei
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Nagendiran, Anuja
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zheng, Haoquan
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zou, Xiaodong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Mesoporous silica nanoparticles applied as a support for Pd and Au nanocatalysts in cycloisomerization reactions2014In: APL materials, ISSN 2166-532X, Vol. 2, no 11, p. 113316-Article in journal (Refereed)
    Abstract [en]

    Ultra-small mesoporous silica nanoparticles (MSNs) have been synthesized at room temperature with particle sizes ranging from 28 to 45 nm. These MSNs have been employed as heterogeneous supports for palladium and gold nanocatalysts. The colloidal nature of the MSNs is highly useful for catalytic applications as it allows for better mass transfer properties and a more uniform distribution of the nanocatalysts in solution. The two nanocatalysts were evaluated in the cycloisomerization of alkynoic acids and demonstrated to produce the corresponding alkylidene lactones in good to excellent yields under mild conditions. In addition to their high activity, the catalysts exhibit low degree of metal leaching and straight-forward recycling, which highlight the practical utility of MSNs as supports for nanocatalysts. (C) 2014 Author(s). All article content, except where otherwise noted, is licensed under a Creative Commons Attribution 3.0 Unported License.

  • 48.
    Verho, Oscar
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Gustafson, Karl P. J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nagendiran, Anuja
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tai, Cheuk-Wai
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mild and Selective Hydrogenation of Nitro Compounds using Palladium Nanoparticles Supported on Amino-Functionalized Mesocellular Foam2014In: ChemCatChem, ISSN 1867-3880, E-ISSN 1867-3899, Vol. 6, no 11, p. 3153-3159Article in journal (Refereed)
    Abstract [en]

    We present the utilization of a heterogeneous catalyst comprised of Pd nanoparticles supported on aminopropyl-functionalized siliceous mesocellular foam (Pd-0-AmP-MCF) for the selective hydrogenation of aromatic, aliphatic, and heterocyclic nitro compounds to the corresponding amines. In general, the catalytic protocol exclusively affords the desired amine products in excellent yields within short reaction times with the reactions performed at room temperature under ambient pressure of H-2. Moreover, the reported Pd nanocatalyst displayed excellent structural integrity for this transformation as it could be recycled multiple times without any observable loss of activity or leaching of metal. In addition, the Pd nanocatalyst could be easily integrated into a continuous-flow device and used for the hydrogenation of 4-nitroanisole on a 2.5 g scale, where the product p-anisidine was obtained in 95% yield within 2 h with a Pd content of less than 1 ppm.

  • 49.
    Verho, Oscar
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nagendiran, Anuja
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Johnston, Eric V.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tai, Cheuk-wai
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nanopalladium on Amino-Functionalized Mesocellular Foam: An Efficient Catalyst for Suzuki Reactions and Transfer Hydrogenations2013In: ChemCatChem, ISSN 1867-3880, E-ISSN 1867-3899, Vol. 5, no 2, p. 612-618Article in journal (Refereed)
    Abstract [en]

    The applications of a heterogeneous Pd0-AmP-MCF nanoparticle catalyst in Suzuki cross-coupling reactions and transfer hydrogenations of alkenes are described. The catalyst was highly efficient for both transformations, resulting in 1)coupling of a wide range of aryl halides with various boronic acids in high yields and 2)chemoselective reduction of a variety of alkenes with the use of 1-methyl-1,4-cyclohexadiene as hydrogen donor. Moreover, the catalyst can be recycled several times without any significant decrease in activity or leaching of metal into solution, making the protocol economical and environmentally friendly. In the case of the Suzuki cross-coupling, a 15-fold increase in reaction rate was observed if the reaction was performed under microwave irradiation compared to conventional heating in an oil bath.

  • 50.
    Xu, Chao
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Afewerki, Samson
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Córdova, Armando
    Hedin, Niklas
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    A Cyclopalladated Microporous Azo-linked Polymer as a Heterogeneous Catalyst for Eco-friendly Suzuki and Heck Coupling ReactionsManuscript (preprint) (Other academic)
12 1 - 50 of 53
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