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  • 1.
    Abdelhamid, Hani Nasser
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Bermejo-Gómez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zou, Xiaodong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    A water-stable lanthanide metal-organic framework for fluorimetric detection of ferric ions and tryptophan2017In: Microchimica Acta, ISSN 0026-3672, E-ISSN 1436-5073, Vol. 184, no 9, p. 3363-3371Article in journal (Refereed)
    Abstract [en]

    The preparation of a highly water stable and porous lanthanide metal-organic framework (MOF) nanoparticles (denoted SUMOF-7II; SU refers to Stockholm University) is described. SUMOF-7II was synthesized starting from the tritopic linker of 2,4,6-tri-p-carboxyphenyl pyridine (H3L2) and La(III) as metal clusters. SUMOF-7II forms a stable dispersion and displays high fluorescence emission with small variation over the pH range of 6 to 12. Its fluorescence is selectively quenched by Fe(III) ions compared to other metal ions. The intensity of the fluorescene emission drops drops linearly in 16.6–167 μM Fe(III) concentration range, and Stern-Volmer plots are linear. The limit of detection (LOD) is 16.6 μM (at an S/N ratio of >3). This indicator probe can also be used for selective detection of tryptophan among several amino acids. Compared to the free linker H3L2, SUMOF-7II offers improved sensitivity and selectivity of the investigated species.

  • 2.
    Abdelhamid, Hani Nasser
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK). Assiut University, Egypt.
    Wilk-Kozubek, Magdalena
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK). PORT Polish Center for Technology Development, Poland.
    El-Zohry, Ahmed M.
    Gómez, Antonio Bermejo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Valiente, Alejandro
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mudring, Anja-Verena
    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).
    Luminescence properties of a family of lanthanide metal-organic frameworks2019In: Microporous and Mesoporous Materials, ISSN 1387-1811, E-ISSN 1873-3093, Vol. 279, p. 400-406Article in journal (Refereed)
    Abstract [en]

    Two isostructural series of lanthanide metal-organic frameworks denoted as SUMOF-7II (Ln) and SUMOF-7IIB (Ln) (Ln = La, Ce, Pr, Nd, Sm, Eu, and Gd) were synthesized using4,4',4 ''-(pyridine-2,4,6-triyl)tris(benzoic acid) (H(3)L2) and a mixture of H(3)L2 and 4,4',4 ''-(benzene-1,3,5-triyl)tris(benzoic acid) (H3BTB) as linkers, respectively. Both series were characterized using powder X-ray diffraction (PXRD), Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), thermal analysis (TGA), and photoluminescence spectroscopy. Photoluminescence measurements show that Eu-MOFs demonstrate a red emission while Pr- and Nd-MOFs display an emission in the near-infrared (NIR) range. On the other hand, La-, Ce-, Sm- and Gd-MOFs exhibit only a ligand-centered emission. The average luminescence lifetimes in the SUMOF-7IIB series are 1.3-1.4-fold longer than the corresponding ones in the SUMOF-7II series. SUMOF-7IIs show a good photo- and thermal stability. Altogether, the properties of SUMOF-7II and SUMOF-7IIB render them promising materials for applications including sensing, biosensing, and telecommunications.

  • 3.
    Abdelhamid, Hani
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Wilk-Kozubek, Magdalena
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Ahmed, M. El-Zohry
    Valiente, Alejandro
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bermejo-Gomez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mudring, Anja-Verena
    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).
    Luminescence Properties for a Family of Highly Stable Lanthanide Metal-Organic FrameworksManuscript (preprint) (Other academic)
  • 4.
    Agrawal, Santosh
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lenormand, Maud
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Selective Alkylation of (Hetero)Aromatic Amines with Alcohols Catalyzed by a Ruthenium Pincer Complex2012In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 14, no 6, p. 1456-1459Article in journal (Refereed)
    Abstract [en]

    A readily available pincer ruthenium(II) complex catalyzes the selective monoalkylation of (hetero)aromatic amines with a wide range of primary alcohols (including pyridine-, furan-, and thiophene-substituted alcohols) with high efficiency when used in low catalyst loadings (1 mol %). Tertiary amine formation via polyalkylation does not occur, making this ruthenium system an excellent catalyst for the synthesis of sec-amines.

  • 5.
    Agrawal, Santosh
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martínez-Castro, Elisa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Marcos, Rocio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Readily Available Ruthenium Complex for Efficient Dynamic Kinetic Resolution of Aromatic alpha-Hydroxy Ketones2014In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 16, no 8, p. 2256-2259Article in journal (Refereed)
    Abstract [en]

    A ruthenium complex formed from commercially available [Ru(p-cymene)Cl-2](2) and 1,4-bis(diphenylphosphino)butane catalyzes the racemization of aromatic alpha-hydroxy ketones very efficiently at room temperature. The racemization is fully compatible with a kinetic resolution catalyzed by a lipase from Pseudomonas stutzeri. This is the first example of dynamic kinetic resolution of alpha-hydroxy ketones at ambient temperature in which the metal and enzyme catalysts work in concert in one pot at room temperature to give quantitative yields of esters of alpha-hydroxy ketones with very high enantioselectivity.

  • 6.
    Ahlsten, Nanna
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bartoszewicz, Agnieszka
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Agrawal, Santosh
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martin-Matute, Belen
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    A facile synthesis of α-fluoro ketones catalyzed by [Cp*IrCl2](2)2011In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, no 16, p. 2600-2608Article in journal (Refereed)
    Abstract [en]

    Allylic alcohols are isomerized into enolates (enols) by [Cp*IrCl2]2. The enolates react with Selectfluor present in the reaction media. This method produces α-fluoro ketones as single constitutional isomers in high yields.

  • 7.
    Ahlsten, Nanna
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bartoszewicz, Agnieszka
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Allylic alcohols as synthetic enolate equivalents: Isomerisation and tandem reactions catalysed by transition metal complexes2012In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 41, no 6, p. 1660-1670Article in journal (Refereed)
    Abstract [en]

    Allylic alcohols can be isomerised into carbonyl compounds by transition metal complexes. In the last few years, catalyst design and development have resulted in highly efficient isomerisations under mild reaction conditions, including enantioselective versions. In addition, the isomerisation of allylic alcohols has been combined with C-C bond forming reactions when electrophiles such as aldehydes or imines were present in the reaction mixture. Also, C-F bonds can be formed when electrophilic fluorinating reagents are used. Thus, allylic alcohols can be treated as latent enol(ate)s. In this article, we highlight the latest developments concerning the isomerisation of allylic alcohols into carbonyl compounds, focusing in particular on tandem isomerisation/C-C or C-heteroatom bond formation processes. Significant attention is given to the mechanistic aspects of the reactions.

  • 8.
    Ahlsten, Nanna
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bermejo Gomez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martin-Matute, Belen
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Iridium-Catalyzed 1,3-Hydrogen Shift/Chlorination of Allylic Alcohols2013In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, no 24, p. 6273-6276Article in journal (Refereed)
  • 9.
    Ahlsten, Nanna
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bermejo-Gómez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of α-chlorinated ketones and aldehydes: Iridium-catalyzed tandem 1,3-H shift/chlorination of allylic alcoholsManuscript (preprint) (Other academic)
  • 10.
    Ahlsten, Nanna
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lundberg, Helena
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martin-Matute, Belen
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rhodium-catalysed isomerisation of allylic alcohols in water at ambient temperature2010In: Green Chemistry, ISSN 1463-9262, E-ISSN 1463-9270, Vol. 12, no 9, p. 1628-1633Article in journal (Refereed)
    Abstract [en]

    An environmentally benign method for the transformation of allylic alcohols into carbonyl compounds is described. Using [Rh(COD(CH3CN)(2)]BF4 (2) in combination with 1,3,5-triaza-7-phosphaadamantane (PTA, 1) as the catalytic system in water results in a very fast redox isomerisation of a variety of secondary allylic alcohols at ambient temperature. Also, some primary allylic alcohols can be isomerised into the corresponding aldehydes. The active complex, which in some cases can be used in catalyst loadings as low as 0.5 mol%, is formed in situ from commercially available reagents. Based on deuterium labelling studies, a tentative mechanism involving metal-enone intermediates is presented.

  • 11.
    Ahlsten, Nanna
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martin-Matute, Belen
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ir-catalysed formation of C-F bonds. From allylic alcohols to α-fluoroketones2011In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 47, no 29, p. 8331-8333Article in journal (Refereed)
    Abstract [en]

    A novel iridium-catalysed tandem isomerisation/C-F bond formation from allylic alcohols and Selectfluor® to prepare α-fluorinated ketones as single constitutional isomers is reported.

  • 12.
    Ahlsten, Nanna
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rhodium-catalysed coupling of allylic, homoallylic, and bishomoallylic alcohols with aldehydes and N-tosylimines2010In: Abstracts of Papers, 239th ACS National Meeting, San Francisco, CA, United States, March 21-25, 2010, American Chemical Society , 2010Conference paper (Other academic)
  • 13.
    Ahlsten, Nanna
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rhodium-catalysed coupling of allylic, homoallylic, and bishomoallylic alcohols with aldehydes and N-tosylimines: insights into the mechanism2009In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 351, no 16, p. 2657-2666Article in journal (Refereed)
    Abstract [en]

    The isomerisation of alkenols followed by reaction with aldehydes or N-tosylimines catalysed by rhodium complexes has been studied. The catalytically active rhodium complex is formed in situ from commercially available (cyclooctadiene)rhodium(l) chloride dimer [Rh(COD)Cl](2). The tandem process affords aldol and Mannich-type products in excellent yields. The key to the success of the coupling reaction is the activation of the catalysts by reaction with postassium tert-butoxide (t-BuOK), which promotes a catalytic cycle via alkoxides rather than rhodium hydrides. This mechanism minimises the formation of unwanted by-products. The mechanism has been studied by (1)H NMR spectroscopy and deuterium labelling experiments.

  • 14.
    Bacsik, Zoltan
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Ahlsten, Nanna
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ziadi, Asraa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Guoying
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Garcia-Bennett, Alfonso E.
    Uppsala universitet.
    Martin-Matute, Belen
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Hedin, Niklas
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Mechanisms and Kinetics for Sorption of CO(2) on Bicontinuous Mesoporous Silica Modified with n-Propylamine2011In: Langmuir, ISSN 0743-7463, E-ISSN 1520-5827, Vol. 27, no 17, p. 11118-11128Article in journal (Refereed)
    Abstract [en]

    We studied equilibrium adsorption and uptake kinetics and identified molecular species that formed during sorption of carbon dioxide on amine-modified silica. Bicontinuous silicas (AMS-6 and MCM-48) were postsynthetically modified with (3-aminopropyl)triethoxysilane or (3-aminopropyl)methyldiethoxysilane, and amine-modified AMS-6 adsorbed more CO(2) than did amine-modified MCM-48. By in situ FTIR spectroscopy, we showed that the amine groups reacted with CO(2) and formed ammonium carbamate ion pairs as well as carbamic acids under both dry and moist conditions. The carbamic acid was stabilized by hydrogen bonds, and ammonium carbamate ion pairs formed preferably on sorbents with high densities of amine groups. Under dry conditions, silylpropylcarbamate formed, slowly, by condensing carbamic acid and silanol groups. The ratio of ammonium carbamate ion pairs to silylpropylcarbamate was higher for samples with high amine contents than samples with low amine contents. Bicarbonates or carbonates did not form under dry or moist conditions. The uptake of CO(2) was enhanced in the presence of water, which was rationalized by the observed release of additional amine groups under these conditions and related formation of ammonium carbamate ion pairs. Distinct evidence for a fourth and irreversibly formed moiety was observed under sorption of CO(2) under dry conditions. Significant amounts of physisorbed, linear CO(2) were detected at relatively high partial pressures of CO(2), such that they could adsorb only after the reactive amine groups were consumed.

  • 15.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ahlsten, Nanna
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martin-Matute, Belen
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Enantioselective Synthesis of Alcohols and Amines by Iridium-Catalyzed Hydrogenation, Transfer Hydrogenation, and Related Processes2013In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 19, no 23, p. 7274-7302Article, review/survey (Refereed)
    Abstract [en]

    The preparation of chiral alcohols and amines by using iridium catalysis is reviewed. The methods presented include the reduction of ketones or imines by using hydrogen (hydrogenations), isopropanol, formic acid, or formate (transfer hydrogenations). Also dynamic and oxidative kinetic resolutions leading to chiral alcohols and amines are included. Selected literature reports from early contributions to December 2012 are discussed.

  • 16.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    González Miera, Greco
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Marcos, Rocio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Norrby, Per-Ola
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mechanistic Studies on the Alkylation of Amines with Alcohols Catalyzed by a Bifunctional Iridium Complex2015In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 5, no 6, p. 3704-3716Article in journal (Refereed)
    Abstract [en]

    The mechanism of the N-alkylation of amines with alcohols catalyzed by an iridium complex containing an N-heterocyclic carbene (NHC) ligand with a tethered alcohol/alkoxide functionality was investigated by a combination of experimental and computational methods. The catalyst resting state is an iridium hydride species containing the amine substrate as a ligand, and decoordination of the amine, followed by coordination of the imine intermediate to the iridium center, constitute the rate-determining step (rds) of the catalytic process. The alcohol/alkoxide that is tethered to the NHC participates in every step of the catalytic cycle by accepting or releasing protons and forming hydrogen bonds with the reacting species. Thus, the iridium complex with the alcohol/alkoxide tethered to the N-heterocyclic carbene ligand acts as a bifunctional catalyst.

  • 17.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jezowska, Martina M.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Laymand, Kevin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mobus, Juri
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of β-Hydroxy and β-Amino Ketones from Allylic Alcohols Catalyzed by Ru(η5-C5Ph5)(CO)2Cl2012In: European Journal of Inorganic Chemistry, ISSN 1434-1948, E-ISSN 1099-1948, no 9, p. 1517-1530Article in journal (Refereed)
    Abstract [en]

    An efficient method for the synthesis of beta-hydroxy and beta-amino ketones from allylic alcohols catalyzed by Ru(5-C5Ph5)(CO)2Cl is described. The influence of the stereoelectronic properties of the catalyst on the reaction outcome has been studied. Optimization of the reaction conditions supressed the formation of undesired side products such as saturated ketones, benzyl alcohols, and a,beta-unsaturated ketones. Several aromatic and aliphatic allylic alcohols have been reacted with a large variety of aldehydes or imines to produce beta-hydroxy ketones or beta-amino ketones, respectively, in yields up to 99%. Based on experimental data, a mechanism via ruthenium alkoxides and ruthenium aldoxides is proposed. In addition, a C-bound ruthenium enolate has been characterized.

  • 18.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Livendahl, Madeleine
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Efficient synthesis of beta-hydroxy ketones from allylic alcohols by catalytic formation of ruthenium enolates2008In: Chemistry: a European Journal, ISSN 0947-6539, Vol. 14, no 34, p. 10547-10550Article in journal (Refereed)
  • 19.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Livendahl, Madeleine
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of b-Hydroxy Ketones from Allylic Alcohols via Catalytic Formation of Ruthenium Enolates2008In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 14, no 34, p. 10547-10550Article in journal (Refereed)
    Abstract [en]

    The most efficient Ru-catalyzed isomerization–aldol reaction from allylic alcohols has been achieved by using [η5-(Ph5Cp)Ru(CO)2Cl] as the catalyst. The bulky pentaphenylcyclopentadienyl ligand on the ruthenium atom prevents protonation at the oxygen of the Ru–enolate intermediate and completely suppresses the formation of unwanted ketone byproducts (see scheme). The domino transformation is as good as it can be: aldols are obtained in quantitative yields at ambient temperature.

  • 20.
    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.

  • 21.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Building molecular complexity via tandem Ru-catalyzed isomerization/C-H activation2009In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 11, no 8, p. 1749-1752Article in journal (Refereed)
    Abstract [en]

    A tandem isomerization/C-H activation of allylic alcohols was performed using a catalytic amount of RUCl(2)(PPh(3))(3). A variety of ortho alkylated ketones have been obtained in excellent yields. This tandem process relies on an in situ generation of a carbonyl functional group that directs the ortho C-H bond activation.

  • 22.
    Bermejo Gómez, Antonio
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ahlsten, Nanna
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Platero-Prats, Ana E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of 4,5-disubstituted 2-aminothiazoles from a,b-unsaturated ketones: Preparation of 5-benzyl-4-methyl-2-aminothiazolium hydrochloride salt2014In: Organic Syntheses, ISSN 0078-6209, Vol. 91, p. 185-200Article in journal (Refereed)
  • 23.
    Bermejo Gómez, Antonio
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Holmberg, Pär
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martin-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Transition metal-catalyzed redox isomerization of codeine and morphine in water2014In: RSC Advances, ISSN 2046-2069, E-ISSN 2046-2069, Vol. 4, no 74, p. 39519-39522Article in journal (Refereed)
    Abstract [en]

    A water-soluble rhodium complex formed from commercially available [Rh(COD)(CH3CN)(2)]BF4 and 1,3,5-triaza-7-phosphaadamantane (PTA) catalyzes the isomerization of both codeine and morphine into hydrocodone and hydromorphone with very high efficiency. The reaction is performed in water, allowing isolation of the final products by simple filtration, which results in very high isolated yields. The reactions can be easily scaled up to 100 g.

  • 24.
    Bermejo-Gómez, Antonio
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ahlsten, Nanna
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of 4,5-disubstituted 2-amino-1,3-thiazoles from α,β-unsaturated ketones: Preparation of 5-Benzyl-4-methyl-1,3-thiazol-2-amine hydrochlorideManuscript (preprint) (Other academic)
  • 25. Bogár, Krisztián
    et al.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Large-scale ruthenium- and enzyme-catalyzed dynamic kinetic resolution of (rac)-1-phenylethanol2007In: Beilstein Journal of Organic Chemistry, ISSN 1860-5397, Vol. 3, p. artikel nr 50-Article in journal (Refereed)
  • 26.
    Carrasco, Sergio
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martin-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Hydrazine-Free Facile Synthesis of Palladium-Tetrakis(Triphenylphosphine)2019In: European Journal of Inorganic Chemistry, ISSN 1434-1948, E-ISSN 1099-1948, no 14, p. 1951-1955Article in journal (Refereed)
    Abstract [en]

    We present an easy and very efficient procedure for the synthesis of Pd(PPh3)(4) using nontoxic reducing agents. The complex is obtained in a remarkable 83 % yield, and the method can be scaled up. A very detailed spectroscopic and spectrometric characterization is reported.

  • 27.
    Carson, Fabian
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Agrawal, Santosh
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Gustafsson, Mikaela
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Bartoszewicz, Agnieszka
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Moraga, Francisca
    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.
    Ruthenium Complexation in an Aluminium Metal-Organic Framework and its Application in Alcohol Oxidation Catalysis2012In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 48, p. 15337-15344Article, review/survey (Refereed)
    Abstract [en]

    A ruthenium trichloride complex has been loaded into an aluminium metalorganic framework (MOF), MOF-253, by post-synthetic modification to give MOF-253-Ru. MOF-253 contains open bipyridine sites that are available to bind with the ruthenium complex. MOF-253-Ru was characterised by elemental analysis, N2 sorption and X-ray powder diffraction. This is the first time that a Ru complex has been coordinated to a MOF through post-synthetic modification and used as a heterogeneous catalyst. MOF-253-Ru catalysed the oxidation of primary and secondary alcohols, including allylic alcohols, with PhI(OAc)2 as the oxidant under very mild reaction conditions (ambient temperature to 40 degrees C). High conversions (up to >99%) were achieved in short reaction times (13 h) by using low catalyst loadings (0.5 mol% Ru). In addition, high selectivities (>90%) for aldehydes were obtained at room temperature. MOF-253-Ru can be recycled up to six times with only a moderate decrease in substrate conversion.

  • 28.
    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.

  • 29.
    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, Rocío
    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).
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Introduction of an N-heterocyclic Carbene Iridium Complex into a Zirconium Metal–Organic Framework for CatalysisManuscript (preprint) (Other academic)
  • 30.
    Carson, Fabian
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Pascanu, Vlad
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bermejo Gómez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhang, Yi
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Platero-Prats, Ana E.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK). Stockholm University, Faculty of Science, Department of Organic Chemistry.
    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.
    Influence of the Base on Pd@MIL-101-NH2(Cr) as Catalyst for the Suzuki-Miyaura Cross-Coupling Reaction2015In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 21, no 30, p. 10896-10902Article in journal (Refereed)
    Abstract [en]

    The chemical stability of metal-organic frameworks (MOFs) is a major factor preventing their use in industrial processes. Herein, it is shown that judicious choice of the base for the Suzuki-Miyaura cross-coupling reaction can avoid decomposition of the MOF catalyst Pd@MIL-101-NH2(Cr). Four bases were compared for the reaction: K2CO3, KF, Cs2CO3 and CsF. The carbonates were the most active and achieved excellent yields in shorter reaction times than the fluorides. However, powder XRD and N-2 sorption measurements showed that the MOF catalyst was degraded when carbonates were used but remained crystalline and porous with the fluorides. XANES measurements revealed that the trimeric chromium cluster of Pd@MIL-101-NH2(Cr) is still present in the degraded MOF. In addition, the different countercations of the base significantly affected the catalytic activity of the material. TEM revealed that after several catalytic runs many of the Pd nanoparticles (NPs) had migrated to the external surface of the MOF particles and formed larger aggregates. The Pd NPs were larger after catalysis with caesium bases compared to potassium bases.

  • 31.
    Cumpstey, Ian
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Agrawal, Santosh
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Borbas, K. Eszter
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Iridium-catalysed condensation of alcohols and amines as a method for aminosugar synthesis2011In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 47, no 27, p. 7827-7829Article in journal (Refereed)
    Abstract [en]

    Primary carbohydrate amines at primary and secondary carbons are alkylated by alcohols in the presence of [Cp*IrCl2]2. When primary carbohydrate alcohols are used as the coupling partners and in the presence of Cs2CO3, amine-linked pseudodisaccharides are obtained. Secondary carbohydrate alcohols are unaffected under these conditions, which allows regioselective reactions.

  • 32.
    Erbing, Elis
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sanz-Marco, Amparo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vazquez-Romero, Ana
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Malmberg, Jesper
    Johansson, Magnus J.
    Gomez-Bengoa, Enrique
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Base- and Additive-Free Ir-Catalyzed ortho-Iodination of Benzoic Acids: Scope and Mechanistic Investigations2018In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 8, no 2, p. 920-925Article in journal (Refereed)
    Abstract [en]

    A protocol for the C-H activation/iodination of benzoic acids catalyzed by a simple iridium complex has been developed. The method described in this paper allows the ortho-selective iodination of a variety of benzoic acids under extraordinarily mild conditions in the absence of any additive or base in 1,1,1,3,3,3-hexafluoroisopropanol as the solvent. The iridium catalyst used tolerates air and moisture, and selectively gives ortho-iodobenzoic acids with high conversions. Mechanistic investigations revealed that an Ir(III)/Ir(V) catalytic cycle operates, and that the unique properties of HFIP enables the C-H iodination using the carboxylic moiety as a directing group.

  • 33.
    Erbing, Elis
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vazquez-Romero, Ana
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bermejo Gómez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Platero-Prats, Ana E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Carson, Fabian
    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).
    Tolstoy, Päivi
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    General, Simple, and Chemoselective Catalysts for the Isomerization of Allylic Alcohols: The Importance of the Halide Ligand2016In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 22, no 44, p. 15659-15663Article in journal (Refereed)
    Abstract [en]

    Remarkably simple Ir-III catalysts enable the isomerization of primary and sec-allylic alcohols under very mild reaction conditions. X-ray absorption spectroscopy (XAS) and mass spectrometry (MS) studies indicate that the catalysts, with the general formula [Cp*Ir-III], require a halide ligand for catalytic activity, but no additives or additional ligands are needed.

  • 34.
    González Miera, Greco
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bermejo Gómez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Chupas, Peter J.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Chapman, Karena W.
    Platero-Prats, Ana E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Topological Transformation of a Metal–Organic Framework Triggered by Ligand Exchange2017In: Inorganic Chemistry, ISSN 0020-1669, E-ISSN 1520-510X, Vol. 56, no 8, p. 4576-4583Article in journal (Refereed)
    Abstract [en]

    Here we describe the topological transformation of the pores of a new framework in the bio-MOF-100 family (dia-c) into the known isomer (lcs) by doubling the pore volume, which occurs during postsynthesis modifications. During this transformation, reassembling of the metal–organic framework (MOF) building blocks into a completely different framework occurs, involving breaking/forming of metal–ligand bonds. MOF crystallinity and local structure are retained, as determined by powder X-ray diffraction (PXRD) and pair distribution function (PDF) analyses, respectively. We exploited the inherent dynamism of bio-MOF-100 by coupling chemical decorations of the framework using solvent-assisted ligand exchange to the topological change. Following this method and starting from the pristine dense dia-c phase, open lcs-bio-MOF-100 was prepared and functionalized in situ with an iridium complex (IrL). Alternatively, the dia-c MOF could be modified with wide-ranging amounts of IrL up to ca. 50 mol %, as determined by solution 1H NMR spectroscopy, by tuning the concentration of the solutions used and with no evidence for isomer transformation. The single-site nature of the iridium complexes within the MOFs was assessed by X-ray absorption spectroscopy (XAS) and PDF analyses. Ligand exchanges occurred quantitatively at room temperature, with no need of excess of the iridium metallolinker.

  • 35.
    González Miera, Greco
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    López, Aitor Bermejo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martínez-Castro, Elisa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Norrby, Per-Ola
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nonclassical Mechanism in the Cyclodehydration of Diols Catalyzed by a Bifunctional Iridium Complex2019In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 25, no 10, p. 2631-2636Article in journal (Refereed)
    Abstract [en]

    1,4- and 1,5-diols undergo cyclodehydration upon treatment with cationic N-heterocyclic carbene (NHC)-Ir-III complexes to give tetrahydrofurans and tetrahydropyrans, respectively. The mechanism was investigated, and a metal-hydride-driven pathway was proposed for all substrates, except for very electron-rich ones. This contrasts with the well-established classical pathways that involve nucleophilic substitution.

  • 36.
    González Miera, Greco
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martínez-Castro, Elisa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Acceptorless Alcohol Dehydrogenation: OH vs NH Effect in Bifunctional NHC–Ir(III) Complexes2018In: Organometallics, ISSN 0276-7333, E-ISSN 1520-6041, Vol. 37, no 5, p. 636-644Article in journal (Refereed)
    Abstract [en]

    Bifunctional complexes bearing N-heterocyclic carbene (NHC) ligands functionalized with hydroxy or amine groups were synthesized to measure the beneficial effect of different modes of metal–ligand cooperation in the acceptorless dehydrogenation of alcohols. In comparison to complexes with an amine moiety, hydroxy-functionalized iridium catalysts showed superior activity. In contrast to alcohols, 1,4-diols underwent cyclization to give the corresponding tetrahydrofurans without involving dehydrogenation processes. Mechanistic investigations to rationalize the “OH effect” in these types of complexes have been undertaken.

  • 37.
    Gustafsson, Mikaela
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Bartoszewicz, Agnieszka
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Grins, Jekabs
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Zhao, Tony
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Li, Zhongyue
    Zhu, Guangshan
    Zou, Xiaodong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    A family of highly stable lanthanide metal-organic frameworks: structural evolution and catalytic activity2010In: Chemistry of Materials, ISSN 0897-4756, E-ISSN 1520-5002, Vol. 22, no 11, p. 3316-3322Article in journal (Refereed)
    Abstract [en]

    A family of homeotypic porous lanthanide metal−organic frameworks (MOFs), [Ln(btc)(H2O)]·guest (Nd (1), Sm (2), Eu (3), Gd (4), Tb (5), Ho (6), Er (7), and Yb (8); guest: DMF or H2O) was synthesized. The structures of the as-synthesized compounds are tetragonal and contain 1D channels with accessible lanthanide ions. In situ single crystal X-ray diffraction shows that 1 undergoes a single-crystal to polycrystalline to single-crystal transformation from room temperature to 180 °C. During the release of DMF and water molecules from the channels by evacuation and subsequent heating, the structures of 1 and 7 transformed from tetragonal to monoclinic, and then to tetragonal, while the structure of 8 remained tetragonal. The transformation between the monoclinic and the low temperature tetragonal phases is reversible. The Ln(btc) MOFs are stable to at least 480 °C and are among the most thermally stable MOFs. The Ln(btc) MOFs act as efficient Lewis acid catalysts for the cyanosilylation of aldehydes yielding cyanohydrins in high yields within short reaction times. 1 also catalyzes the cyanosilylation of less reactive substrates, such as ketones at room temperature. The Ln(btc) MOFs could be recycled and reused without loss of their crystallinity and activity.

  • 38. Hernández-Toribio, Jorge
    et al.
    Gómez Arrayás, Ramón
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Carretero, Juan C.
    Catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides with α,β-unsaturated ketones2009In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 11, no 2, p. 393-396Article in journal (Refereed)
  • 39. Mahanti, Bani
    et al.
    González Miera, Greco
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martínez-Castro, Elisa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bedin, Michele
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ott, Sascha
    Thapper, Anders
    Homogeneous Water Oxidation by Half-Sandwich Iridium(III) N-Heterocyclic Carbene Complexes with Pendant Hydroxy and Amino Groups2017In: ChemSusChem, ISSN 1864-5631, E-ISSN 1864-564X, Vol. 10, no 22, p. 4616-4623Article in journal (Refereed)
    Abstract [en]

    Herein, we report three (IrCp)-Cp-III* complexes with hydroxy-or amino-functionalized N-heterocyclic carbene (NHC) ligands that catalyze efficient water oxidation induced by addition of ceric ammonium nitrate (CAN). The pendant hydroxy or amino groups are very important for activity, and the complexes with heteroatom-functionalized NHC ligands show up to 15 times higher rates of oxygen evolution in CAN-induced water oxidation than a reference (IrCp)-Cp-III* complex without heteroatom functionalization. The formation of molecular high-valent Ir intermediates that are presumably involved in the rate-determining step for water oxidation is established by UV/Vis spectroscopy and ESI-MS under turnover conditions. The hydroxy groups on the NHC ligands, as well as chloride ligands on the iridium center are proposed to structurally stabilize the highvalent species, and thereby improve the catalytic activity. The Ir-III complex with a hydroxy-functionalized NHC shows the highest catalytic activity with a TON of 2500 obtained in 3 h and with >90% yield relative to the amount of oxidant used.

  • 40.
    Marcos, Rocio
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Combined Enzyme and Transition-Metal Catalysis for Dynamic Kinetic Resolutions2012In: Israel Journal of Chemistry, ISSN 0021-2148, Vol. 52, no 7, p. 639-652Article, review/survey (Refereed)
    Abstract [en]

    The preparation of optically pure alcohols, axially chiral allenes, and amine derivatives by using enzymes and transition-metal catalysts through dynamic kinetic resolution (DKR) is reviewed. After a general introduction into enzymatic kinetic resolutions and racemizations catalyzed by transition-metal complexes, selected examples of DKRs are presented, from early work to more recent outstanding contributions, and also applications of this approach.

  • 41.
    Martinez-Erro, Samuel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bermejo Gómez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vazquez-Romero, Ana
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Erbing, Elis
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    2,2-Diiododimedone: a mild electrophilic iodinating agent for the selective synthesis of alpha-iodoketones from allylic alcohols2017In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 53, no 71, p. 9842-9845Article in journal (Refereed)
    Abstract [en]

    2,2-Diiodo-5,5-dimethylcyclohexane-1,3-dione is reported as a new electrophilic iodinating agent that selectively iodinates electron-rich aromatics. In contrast to other common electrophilic iodinating reagents, its mild nature allows it to be used for the selective synthesis of alpha-iodinated carbonyl compounds from allylic alcohols through a 1,3-hydrogen shift/iodination process catalyzed by iridium(III) complexes.

  • 42.
    Martinez-Erro, Samuel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sanz-Marco, Amparo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bermejo Gómez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vazquez-Romero, Ana
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ahlquist, Mårten S. G.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Base-Catalyzed Stereospecific Isomerization of Electron-Deficient Allylic Alcohols and Ethers through Ion-Pairing2016In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 138, no 40, p. 13408-13414Article in journal (Refereed)
    Abstract [en]

    A mild base-catalyzed strategy for the isomerization of allylic alcohols and allylic ethers has been developed. Experimental and computational investigations indicate that transition metal catalysts are not required when basic additives are present. As in the case of using transition metals under basic conditions, the isomerization catalyzed solely by base also follows a stereospecific pathway. The reaction is initiated by a rate-limiting deprotonation. Formation of an intimate ion pair between an allylic anion and the conjugate acid of the base results in efficient transfer of chirality. Through this mechanism, stereochemical information contained in the allylic alcohols is transferred to the ketone products. The stereospecific isomerization is also applicable for the first time to allylic ethers, yielding synthetically valuable enantioenriched (up to 97% ee) enol ethers.

  • 43.
    Martín-Matute, Belén
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bartoszewicz, Agnieszka
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ahlsten, Nanna
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tandem transformations of allylic alcohols using transition metal complexes2010In: Abstracts of Papers, 239th ACS National Meeting, San Francisco, CA, United States, March 21-25, 2010, American Chemical Society , 2010Conference paper (Other academic)
  • 44.
    Martín-Matute, Belén
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bogár, Krisztián
    Edin, Michaela
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kaynak, F. Betül
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Highly efficient redox isomerization of allylic alcohols at ambient temperature catalyzed by novel ruthenium cyclopentadienyl complexes: New insight into the mechanism2005In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 11, no 20, p. 5832-5842Article in journal (Refereed)
    Abstract [en]

    A range of ruthenium cyclopentadienyl (Cp) complexes have been prepared and used for isomerization of allylic alcohols to the corresponding saturated carbonyl compounds. Complexes bearing CO ligands show higher activity than those with PPh3 ligands. The isomerization rate is highly affected by the substituents on the Cp ring. Tetra(phenyl)methyl-substituted catalysts rapidly isomerize allylic alcohols under very mild reaction conditions (ambient temperature) with short reaction times. Substituted allylic alcohols have been isomerized by employing Ru–Cp complexes. A study of the isomerization catalyzed by [Ru(Ph5Cp)(CO)2H] (14) indicates that the isomerization catalyzed by ruthenium hydrides partly follows a different mechanism than that of ruthenium halides activated by KOtBu. Furthermore, the lack of ketone exchange when the isomerization was performed in the presence of an unsaturated ketone (1 equiv), different from that obtained by dehydrogenation of the starting allylic alcohol, supports a mechanism in which the isomerization takes place within the coordination sphere of the ruthenium catalyst.

  • 45.
    Martín-Matute, Belén
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Chemoenzymatic deracemization processes2008In: Organic Synthesis with Enzymes in Non-Aqueous Media, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim , 2008, p. 113-144Chapter in book (Refereed)
  • 46.
    Martín-Matute, Belén
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dynamic kinetic resolutions2008In: Asymmetric Organic Synthesis with Enzymes, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim , 2008, p. 89-113Chapter in book (Refereed)
  • 47.
    Martín-Matute, Belén
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Edin, Michaela
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bogár, Krisztián
    Kaynak, F. Betül
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Combined ruthenium(II)- and lipase catalysis for efficient dynamic kinetic resolution of sec-alcohols. Insight into a new racemization mechanism2005In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 127, no 24, p. 8817-8825Article in journal (Refereed)
    Abstract [en]

     

    Pentaphenylcyclopentadienyl ruthenium complexes (3) are excellent catalysts for the racemization of secondary alcohols at ambient temperature. The combination of this process with enzymatic resolution of the alcohols results in a highly efficient synthesis of enantiomerically pure acetates at room temperature with short reaction times for most substrates. This new reaction was applied to a wide range of functionalized alcohols including heteroaromatic alcohols, and for many of the latter, enantiopure acetates were efficiently prepared for the first time via dynamic kinetic resolution (DKR). Different substituted cyclopentadienyl ruthenium complexes were prepared and studied as catalysts for racemization of alcohols. Pentaaryl-substituted cyclopentadienyl complexes were found to be highly efficient catalysts for the racemization. Substitution of one of the aryl groups by an alkyl group considerably slows down the racemization process. A study of the racemization of (S)-1-phenylethanol catalyzed by ruthenium hydride η5-Ph5CpRu(CO)2H (8) indicates that the racemization takes place within the coordination sphere of the ruthenium catalyst. This conclusion was supported by the lack of ketone exchange in the racemization of (S)-1-phenylethanol performed in the presence of p-tolyl methyl ketone (1 equiv), which gave <1% of 1-(p-tolyl)ethanol. The structures of ruthenium chloride and iodide complexes 3a and 3c and of ruthenium hydride complex 8 were confirmed by X-ray analysis.

  • 48.
    Martín-Matute, Belén
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mitchell, Terence N.
    6. Organotin Reagents in Cross-Coupling Reactions2014In: Metal-Catalyzed Cross-Coupling Reactions and More / [ed] Armin de Meijere, Stefan Bräse, Martin Oestreich, Weinheim: Wiley-VCH Verlagsgesellschaft, 2014, 1, p. 423-474Chapter in book (Refereed)
  • 49.
    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.

  • 50.
    Pascanu, Vlad
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bermejo Gómez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ayats, Carles
    Platero-Prats, Ana E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Carson, Fabian
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Su, Jie
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Yao, Qingxia
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Pericas, Miquel A.
    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.
    Double-Supported Silica-Metal-Organic Framework Palladium Nanocatalyst for the Aerobic Oxidation of Alcohols under Batch and Continuous Flow Regimes2015In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 5, no 2, p. 472-479Article in journal (Refereed)
    Abstract [en]

    Stable and easily synthesized metal-organic framework MIL-88B-NH2 represents an attractive support for catalysts employed in oxidation reactions, which are typically performed under relatively harsh conditions. However, MIL-88B-NH2, the thermodynamic polymorph of the more popular MIL-101-NH2, has been rarely employed in catalytic applications because of a difficult impregnation process caused by the flexible nature of the framework. We report herein a new catalyst denoted Pd@MIL-88B-NH2 (8 wt % Pd), the first example of metallic nanoparticles successfully impregnated in the pores of MIL-88B-NH2. Furthermore, by enclosing the MOF crystals in a tailored protective coating of SiO2 nanoparticles, an even more enduring material was developed and applied to the aerobic oxidation of benzylic alcohols. This doubly supported catalyst Pd@MIL-88B-NH2@nano-SiO2 displayed high activity and excellent performance in terms of endurance and leaching control. Under batch conditions, a very convenient and efficient recycling protocol is illustrated, using a teabag approach. Under continuous flow, the catalyst was capable of withstanding 7 days of continuous operation at 110 degrees C without deactivation. During this time, no leaching of metallic species was observed, and the material maintained its structural integrity.

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