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  • 51. Liu, Yanna
    et al.
    Richardson, Evan S.
    Derocher, Andrew E.
    Lunn, Nicholas J.
    Lehmler, Hans-Joachim
    Li, Xueshu
    Zhang, Yifeng
    Cui, Julia Yue
    Cheng, Lihua
    Martin, Jonathan W.
    Stockholm University, Faculty of Science, Department of Environmental Science and Analytical Chemistry. Stockholm University, Science for Life Laboratory (SciLifeLab). University of Alberta, Canada.
    Hundreds of Unrecognized Halogenated Contaminants Discovered in Polar Bear Serum2018In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 57, no 50, p. 16401-16406Article in journal (Refereed)
    Abstract [en]

    Exposure of polar bears (Ursus maritimus) to persistent organic pollutants was discovered in the 1970s, but recent evidence suggests the presence of unknown toxic chemicals in their blood. Protein and phospholipid depleted serum was stirred with polyethersulfone capillaries to extract a broad range of analytes, and nontarget mass spectrometry with fragmentation flagging was used for detection. Hundreds of analytes were discovered belonging to 13 classes, including novel polychlorinated biphenyl (PCB) metabolites and many fluorinated or chlorinated substances not previously detected. All analytes were detected in the oldest (mid-1980s) archived polar bear serum from Hudson Bay and Beaufort Sea, and all fluorinated classes showed increasing trends. A mouse experiment confirmed the novel PCB metabolites, suggesting that these could be widespread in mammals. Historical exposure and toxic risk has been underestimated, and these halogenated contaminants pose uncertain risks to this threatened species.

  • 52. Liu, Yong
    et al.
    Jia, Chun-Jiang
    Yamasaki, Jun
    Terasaki, Osamu
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Schueth, Ferdi
    Highly Active Iron Oxide Supported Gold Catalysts for CO Oxidation: How Small Must the Gold Nanoparticles Be?2010In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 49, no 33, p. 5771-5775Article in journal (Refereed)
  • 53. Ma, Guangning
    et al.
    Afewerki, Samson
    Deiana, Luca
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palo-Nieto, Carlos
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Liu, Leifeng
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Inorganic and Structural Chemistry.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Inorganic and Structural Chemistry.
    Ibrahem, Ismail
    Cordova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    A Palladium/Chiral Amine Co-catalyzed Enantioselective Dynamic Cascade Reaction: Synthesis of Polysubstituted Carbocycles with a Quaternary Carbon Stereocenter2013In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, no 23, p. 6050-6054Article in journal (Refereed)
  • 54. Martín-Matute, Belén
    et al.
    Edin, Michaela
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bogár, Krisztián
    Bäckvall, Jan-E.
    Highly compatible metal and enzyme catalysts for efficient dynamic kinetic resolution of alcohols at ambient temperature2004In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 43, p. 6535-6539Article in journal (Refereed)
  • 55. Men, Yong-Biao
    et al.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry.
    Huang, Zhi-Tang
    Zheng, Qi-Yu
    Rational Construction of 2D and 3D Borromean Arrayed Organic Crystals by Hydrogen Bonds Directed Self-Assembly2009In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 48, no 16, p. 2873-2876Article in journal (Refereed)
    Abstract [en]

    The Borromean system, which contains nontrivial three ring links (no ring is interlocked to another without the help of the third one), is a very intriguing pattern of crystal entanglements, because of the topological complexity, structural integrity, and aesthetic beauty. Herein we report the rational construction of Borromean three-fold 2D-2D entangled layers and n-Borromean 2D-3D entangled infinite layers with pure organic supramolecular synthons based on hydrogen-bond-directed self assembly.

  • 56. Meng, Yi
    et al.
    Luo, Yi
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK). Peking University, China.
    Shi, Ji-Long
    Ding, Huimin
    Lang, Xianjun
    Chen, Wei
    Zheng, Anmin
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK). Peking University, China.
    Wang, Cheng
    2D and 3D Porphyrinic Covalent Organic Frameworks: The Influence of Dimensionality on Functionality2020In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 59, no 9, p. 3624-3629Article in journal (Refereed)
    Abstract [en]

    The construction of 2D and 3D covalent organic frameworks (COFs) from functional moieties for desired properties has gained much attention. However, the influence of COFs dimensionality on their functionalities, which can further assist in COF design, has never been explored. Now, by selecting designed precursors and topology diagrams, 2D and 3D porphyrinic COFs (2D-PdPor-COF and 3D-PdPor-COF) are synthesized. By model building and Rietveld refinement of powder X-ray diffraction, 2D-PdPor-COF crystallizes as 2D sheets while 3D-PdPor-COF adopts a five-fold interpenetrated pts topology. Interestingly, compared with 2D-PdPor-COF, 3D-PdPor-COF showed interesting properties, including 1) higher CO2 adsorption capacity; 2) better photocatalytic performance; and 3) size-selective photocatalysis. Based on this study, we believe that with the incorporation of functional moieties, the dimensionality of COFs can definitely influence their functionalities.

  • 57.
    Merritt, Eleanor A.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Diaryliodonium salts: A journey from obscurity to fame2009In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 48, no 48, p. 9052-9070Article, review/survey (Refereed)
    Abstract [en]

    The recent groundbreaking developments in the application of diaryliodonium salts in cross-coupling reactions has brought this class of previously underdeveloped reagents to the forefront of organic chemistry. With the advent of novel, facile, and efficient synthetic routes to these compounds, many more applications can be foreseen. Herein we provide an overview of the historical and recent advances in the synthesis and applications of diaryliodonium salts.

  • 58. Miralles, Nuria
    et al.
    Alam, Rauful
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Fernandez, Elena
    Transition-Metal-Free Borylation of Allylic and Propargylic Alcohols2016In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, no 13, p. 4303-4307Article in journal (Refereed)
    Abstract [en]

    The base-catalyzed allylic borylation of tertiary allylic alcohols allows the synthesis of 1,1-disubstituted allyl boronates, in moderate to high yield. The unexpected tandem performance of the Lewis acid-base adduct, [Hbase](+)[MeO-B(2)pin(2)](-) favored the formation of 1,2,3-triborylated species from the tertiary allylic alcohols and 1-propargylic cyclohexanol at 90 degrees C.

  • 59.
    Miyasaka, Keiichi
    et al.
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry.
    Han, Lu
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry.
    Che, Shunai
    Terasaki, Osamu
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry.
    A lesson from the unusual morphology of silica mesoporous crystals: Growth and close packing of spherical micelles with multiple twinning2006In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 45, no 39, p. 6516-6519Article in journal (Refereed)
  • 60. Miyasaka, Keiichi
    et al.
    Terasaki, Osamu
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Self-Consistent Structural Solution of Mesoporous Crystals by Combined Electron Crystallography and Curvature Assessment2010In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 49, no 47, p. 8867-8871Article in journal (Refereed)
  • 61.
    Montesinos-Magraner, Marc
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Costantini, Matteo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ramírez-Contreras, Rodrigo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Muratore, Michael E.
    Johansson, Magnus J.
    Mendoza, Abraham
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    General Cyclopropane Assembly by Enantioselective Transfer of a Redox-Active Carbene to Aliphatic Olefins2019In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, no 18, p. 5930-5935Article in journal (Refereed)
    Abstract [en]

    Asymmetric cyclopropane synthesis currently requires bespoke strategies, methods, substrates, and reagents, even when targeting similar compounds. This approach slows down discovery and limits available chemical space. Introduced herein is a practical and versatile diazocompound and its performance in the first unified asymmetric synthesis of functionalized cyclopropanes. The redox-active leaving group in this reagent enhances the reactivity and selectivity of geminal carbene transfer. This effect allowed the asymmetric cyclopropanation of various olefins, including unfunctionalized aliphatic alkenes, that enables the three-step total synthesis of (-)-dictyoptereneA. This unified synthetic approach delivers high enantioselectivities that are independent of the stereoelectronic properties of the functional groups transferred. Our results demonstrate that orthogonally differentiated diazocompounds are viable and advantageous equivalents of single-carbon chirons.

  • 62.
    Naidu, Veluru Ramesh
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Posevins, Daniels
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Volla, Chandra M. R.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Selective Cascade Reaction of Bisallenes via Palladium-Catalyzed Aerobic Oxidative Carbocyclization-Borylation and Aldehyde Trapping2017In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 6, p. 1590-1594Article in journal (Refereed)
    Abstract [en]

    A cascade reaction, consisting of a palladium-catalyzed regioselective aerobic oxidative carbocyclization-borylation of bisallenes and a final aldehyde trapping, afforded triene alcohols with high diastereoselectivity. The cascade reaction occurs under mild reaction conditions and proceeds via an allylboron intermediate that is trapped by the aldehyde in a stereoselective manner.

  • 63.
    Niclas, Solin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kjellgren, Johan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-Catalyzed Electrophilic Substitution via Monoallylpalladium Intermediates2003In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 42, no 31, p. 3656-3658Article in journal (Refereed)
  • 64.
    Nyhlén, Jonas
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Duan, Lele
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Licheng
    Privalov, Timofei
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Evolution of O2 in a seven-coordinate RuIV dimer complex with a [HOHOH]- bridge: A computational study2010In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 49, no 10, p. 1773-1777Article in journal (Refereed)
  • 65.
    Olsson, Vilhelm J.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Selective one-pot carbon-carbon bond formation by catalytic boronation of unactivated cycloalkenes and subsequent coupling2007In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 46, no 36, p. 6891-6893Article in journal (Refereed)
  • 66. Orwick, Marcella C.
    et al.
    Judge, Peter J.
    Procek, Jan
    Lindholm, Ljubica
    Stockholm University, Faculty of Science, Department of Biochemistry and Biophysics.
    Graziadei, Andrea
    Engel, Andreas
    Grobner, Gerhard
    Watts, Anthony
    Detergent-Free Formation and Physicochemical Characterization of Nanosized Lipid-Polymer Complexes: Lipodisq2012In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 51, no 19, p. 4653-4657Article in journal (Refereed)
  • 67.
    Otero-Fraga, Jorge
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Suárez-Pantiga, Samuel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Montesinos-Magraner, Marc
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rhein, Dennis
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mendoza, Abraham
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Direct and Stereospecific [3+2] Synthesis of Pyrrolidines from Simple Unactivated Alkenes2017In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 42, p. 12962-12966Article in journal (Refereed)
    Abstract [en]

    Pyrrolidines are important heterocyclic compounds with endless applications in organic synthesis, metal catalysis, and organocatalysis. Their potential as ligands for first-row transition-metal catalysts inspired a new method to access complex poly-heterocyclic pyrrolidines in one step from available materials. This fundamental step forward is based on the discovery of an essential organoaluminum promoter that engages unactivated and electron-rich olefins in intermolecular [3+2] cycloadditions.

  • 68. Pan, Qinhe
    et al.
    Li, Jiyang
    Christensen, Kirsten Elvira
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry.
    Bonneau, Charlotte
    Ren, Xiaoyan
    Shi, Lei
    Zou, Xiaodong
    Li, Guanghua
    Yu, Jihong
    Xu, Ruren
    A germanate built from from 68126 cavity co-templated by a (H2O)16 water cluster and 2-methylpiperazine2008In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773Article in journal (Refereed)
  • 69.
    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.

  • 70. Payer, Stefan E.
    et al.
    Marshall, Stephen A.
    Bärland, Natalie
    Sheng, Xiang
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Reiter, Tamara
    Dordic, Andela
    Steinkellner, Georg
    Wuensch, Christiane
    Kaltwasser, Susann
    Fisher, Karl
    Rigby, Stephen E. J.
    Macheroux, Peter
    Vonck, Janet
    Gruber, Karl
    Faber, Kurt
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Leys, David
    Pavkov-Keller, Tea
    Glueck, Silvia M.
    Regioselective para-Carboxylation of Catechols with a Prenylated Flavin Dependent Decarboxylase2017In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 44, p. 13893-13897Article in journal (Refereed)
    Abstract [en]

    The utilization of CO2 as a carbon source for organic synthesis meets the urgent demand for more sustainability in the production of chemicals. Herein, we report on the enzyme-catalyzed para-carboxylation of catechols, employing 3,4-dihydroxybenzoic acid decarboxylases (AroY) that belong to the UbiD enzyme family. Crystal structures and accompanying solution data confirmed that AroY utilizes the recently discovered prenylated FMN (prFMN) cofactor, and requires oxidative maturation to form the catalytically competent prFMN(iminium) species. This study reports on the in vitro reconstitution and activation of a prFMN-dependent enzyme that is capable of directly carboxylating aromatic catechol substrates under ambient conditions. A reaction mechanism for the reversible decarboxylation involving an intermediate with a single covalent bond between a quinoid adduct and cofactor is proposed, which is distinct from the mechanism of prFMN-associated 1,3-dipolar cycloadditions in related enzymes.

  • 71.
    Persson, Andreas K. A.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jiang, Tuo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Johnson, Magnus T.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-Catalyzed Oxidative Borylative Carbocyclization of Enallenes2011In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, no 27, p. 6155-6159Article in journal (Refereed)
    Abstract [en]

    An efficient oxidative carbocyclization/borylation of enallenes uses Pd(OAc)2 as the catalyst, B2pin2 as the boron-transfer reagent, and 1,4-benzoquinone (BQ) as the oxidant (see scheme). The reaction seems to take place through activation of the allene by a PdII complex to give an alkenyl–PdII intermediate followed by carbopalladation of the olefin and subsequent cleavage of the intermediate palladium–carbon bond by the boron reagent.

  • 72.
    Persson, Andreas K. Å.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium(II)-catalyzed oxidative carbocyclization of aza-enallenes2010In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 49, no 27, p. 4624-4627Article in journal (Refereed)
    Abstract [en]

    Live and let diene: A palladium(II)-catalyzed oxidative carbocyclization reaction of aza-enallenes provides access to potentially valuable heterocyclic dienes. In the presence of a dieneophile during the carbocyclization step, the products can react further in a one-pot cyclization/Diels–Alder sequence to give polycyclic products. BQ=para-benzoquinone

  • 73.
    Pilarski, Lukasz T.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabo, Kalman J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-Catalyzed Direct Synthesis of Organoboronic Acids2011In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, no 36, p. 8230-8232Article in journal (Refereed)
  • 74.
    Ponra, Sudipta
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Yang, Jianping
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kerdphon, Sutthichat
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Andersson, Pher G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry. University of KwaZulu-Natal, South Africa.
    Asymmetric Synthesis of Alkyl Fluorides: Hydrogenation of Fluorinated Olefins2019In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, no 27, p. 9282-9287Article in journal (Refereed)
    Abstract [en]

    The development of new general methods for the synthesis of chiral fluorine-containing molecules is important for several scientific disciplines. We herein disclose a straightforward method for the preparation of chiral organofluorine molecules that is based on the iridium-catalyzed asymmetric hydrogenation of trisubstituted alkenyl fluorides. This catalytic asymmetric process enables the synthesis of chiral fluorine molecules with or without carbonyl substitution. Owing to the tunable steric and electronic properties of the azabicyclo thiazole-phosphine iridium catalyst, this stereoselective reaction could be optimized and was found to be compatible with various aromatic, aliphatic, and heterocyclic systems with a variety of functional groups, providing the highly desirable products in excellent yields and enantioselectivities.

  • 75. Puhakainen, Kati
    et al.
    Benson, Daryn
    Nylén, Johanna
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Konar, Sumit
    Arizona State University, USA.
    Stoyanov, Emil
    Leinenweber, Kurt
    Häussermann, Ulrich
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Hypervalent octahedral SiH62- species from high pressure synthesis2012In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 51, no 13, p. 3156-3160Article in journal (Refereed)
  • 76.
    Purkait, Nibadita
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kervefors, Gabriella
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Linde, Erika
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Regiospecific N-Arylation of Aliphatic Amines under Mild and Metal-Free Reaction Conditions2018In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 57, no 35, p. 11427-11431Article in journal (Refereed)
    Abstract [en]

    A transition metal-free N-arylation of primary and secondary amines with diaryliodonium salts is presented. Both acyclic and cyclic amines are well tolerated, providing a large set of N-alkyl anilines. The methodology is unprecedented among metal-free methods in terms of amine scope, the ability to transfer both electron-withdrawing and electron-donating aryl groups, and efficient use of resources, as excess substrate or reagents are not required.

  • 77.
    Qiu, Youai
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Posevins, Daniels
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Selective Palladium-Catalyzed Allenic C-H Bond Oxidation for the Synthesis of [3]Dendralenes2017In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 42, p. 13112-13116Article in journal (Refereed)
    Abstract [en]

    A highly selective palladium-catalyzed allenic C-H bond oxidation was developed, and it provides a novel and straightforward synthesis of [3]dendralene derivatives. A variety of [3]dendralenes with diverse substitution patterns are accessible with good efficiency and high stereoselectivity. The reaction tolerates a broad substrate scope containing various functional groups on the allene moiety, including ketone, aldehyde, ester, and phenyl groups. Also, a wide range of olefins with both electron-donating and electron-withdrawing aryls, acrylate, sulfone, and phosphonate groups are tolerated.

  • 78.
    Qiu, Youai
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Yang, Bin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jiang, Tuo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhu, Can
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-Catalyzed Oxidative Cascade Carbonylative Spirolactonization of Enallenols2017In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 56, no 12, p. 3221-3225Article in journal (Refereed)
    Abstract [en]

    A highly selective palladium-catalyzed oxidative carbonylation/carbocyclization/alkoxycarbonylation of enallenols to afford spirolactones bearing an all-carbon quaternary center was developed. This transformation involves the overall formation of three C-C bonds and one C-O bond through a cascade insertion of carbon monoxide (CO), an olefin, and CO. Preliminary experiments on chiral anion-induced enantioselective carbonylation/carbocyclization of enallenols afforded spirolactones with moderate enantioselectivity.

  • 79.
    Qiu, Youai
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Yang, Bin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhu, Can
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-Catalyzed Oxidative Carbocyclization–Borylation of Enallenes to Cyclobutenes2016In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, no 22, p. 6520-6524Article in journal (Refereed)
    Abstract [en]

    A highly efficient palladium-catalyzed oxidative borylation of enallenes was developed for the selective formation of cyclobutene derivatives and fully-substituted alkenylboron compounds. Cyclobutenes are formed as the exclusive products in MeOH in the presence of H2O and Et3N, whereas the use of AcOH leads to alkenylboron compounds. Both reactions showed a broad substrate scope and good tolerance for various functional groups, including carboxylic acid ester, free hydroxy, imide, and alkyl groups. Furthermore, transformations of the borylated products were conducted to show their potential applications.

  • 80.
    Raducan, Mihai
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Alam, Rauful
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabo, Kalman J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-Catalyzed Synthesis and Isolation of Functionalized Allylboronic Acids: Selective, Direct Allylboration of Ketones2012In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 51, no 52, p. 13050-13053Article in journal (Refereed)
  • 81.
    Reitti, Marcus
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Villo, Piret
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    One-Pot C-H Functionalization of Arenes by Diaryliodonium Salts2016In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, no 31, p. 8928-8932Article in journal (Refereed)
    Abstract [en]

    A transition-metal-free, mild, and highly regioselective synthesis of nitroarenes from arenes has been developed. The products are obtained in a sequential one-pot reaction by nitration of iodine(III) reagents with two carbon ligands, which are formed in situ from iodine(I). This novel concept has been extended to formation of aryl azides, and constitutes an important step towards catalytic reactions with these hypervalent iodine reagents. An efficient nitration of isolated diaryl-iodonium salts has also been developed, and the mechanism is proposed to proceed by a [2,2] ligand coupling pathway.

  • 82. Sapu, Chicco Manzuna
    et al.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Deska, Jan
    Enantioselective Enzymatic Desymmetrization of Prochiral Allenic Diols2011In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, no 41, p. 9731-9734Article in journal (Refereed)
  • 83. Schaefer, Bernhard
    et al.
    Oeberg, Elisabet
    Kritikos, Mikael
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Inorganic and Structural Chemistry.
    Ott, Sascha
    Incorporating Phosphaalkenes into Oligoacetylenes2008In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 47, no 43, p. 8228-8231Article in journal (Refereed)
  • 84.
    Selander, Nicklas
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Willy, Benjamin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Selective C-H Borylation of Alkenes by Palladium Pincer Complex Catalyzed Oxidative Functionalization2010In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 49, no 24, p. 4051-4053Article in journal (Refereed)
  • 85. Seo, Seungwan
    et al.
    Yang, Taimin
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Shin, Jiho
    Jo, Donghui
    Zou, Xiaodong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Hong, Suk Bong
    Two Aluminophosphate Molecular Sieves Built from Pairs of Enantiomeric Structural Building Units2018In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 57, no 14, p. 3727-3732Article in journal (Refereed)
    Abstract [en]

    Herein we report the synthesis and structures of two new small-pore aluminophosphate molecular sieves PST-13 and PST-14 with mutually connected 8-ring channels. The structure of PST-13, synthesized using diethylamine as an organic structure-directing agent, contains penta-coordinated framework Al atoms bridged by hydroxy groups and thus edge-sharing 3- and 5-rings. Upon calcination, PST-13 undergoes a transformation to PST-14 with loss of bridging hydroxy groups and occluded organic species. The structures of both materials consist nonjointly of pairs of previously undiscovered 1,5- and 1,6-open double 4-rings (d4rs) which are mirror images of each other. We also present a series of novel chemically feasible hypothetical structures built from 1-open d4r (sti) or 1,3-open d4r (nsc) units, as well as from these two enantiomeric structural building units.

  • 86. Shin, Jiho
    et al.
    Xu, Hongyi
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Seo, Seungwan
    Peng, Guo
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Gi Min, Jung
    Cho, Jung
    Wright, Paul A.
    Zou, Xiaodong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Hong, Suk Bong
    Targeted Synthesis of Two Super-Complex Zeolites with Embedded Isoreticular Structures2016In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, no 16, p. 4928-4932Article in journal (Refereed)
    Abstract [en]

    A novel structural coding approach combining structure solution, prediction, and the targeted synthesis of new zeolites with expanding complexity and embedded isoreticular structures was recently proposed. Using this approach, the structures of two new zeolites in the RHO family, PST-20 and PST-25, were predicted and synthesized. Herein, by extending this approach, the next two higher generation members of this family, PST-26 and PST-28, have been predicted and synthesized. These two zeolites have much larger unit cell volumes (422 655 Å3 and 614 912 Å3, respectively) than those of the lower generations. Their crystallization was confirmed by a combination of both powder X-ray and electron diffraction techniques. Aluminate and water concentrations in the synthetic mixture were found to be the two most critical factors influencing the structural expansion of embedded isoreticular zeolites under the synthetic conditions studied herein.

  • 87. Smeets, Stef
    et al.
    Xie, Dan
    Baerlocher, Christian
    McCusker, Lynne B.
    Wan, Wei
    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).
    Zones, Stacey I.
    High-Silica Zeolite SSZ-61 with Dumbbell-Shaped Extra-Large-Pore Channels2014In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 53, no 39, p. 10398-10402Article in journal (Refereed)
    Abstract [en]

    The synthesis of the high-silica zeolite SSZ-61 using a particularly bulky polycyclic structure-directing agent and the subsequent elucidation of its unusual framework structure with extra-large dumbbell-shaped pore openings are described. By using information derived from a variety of X-ray powder diffraction and electron microscopy techniques, the complex framework structure, with 20 Si atoms in the asymmetric unit, could be determined and the full structure refined. The Si atoms at the waist of the dumbbell are only three-connected and are bonded to terminal O atoms pointing into the channel. Unlike the six previously reported extra-large-pore zeolites, SSZ-61 contains no heteroatoms in the framework and can be calcined easily. This, coupled with the possibility of inserting a catalytically active center in the channel between the terminal O atoms in place of H+, afford SSZ-61 intriguing potential for catalytic applications.

  • 88.
    Smeets, Stef
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK). Delft University of Technology, The Netherlands.
    Zones, Stacey I.
    Xie, Dan
    Palatinus, Lukas
    Pascual, Jesus
    Hwang, Son-Jong
    Schmidt, Joel E.
    McCusker, Lynne B.
    SSZ-27: A Small-Pore Zeolite with Large Heart-Shaped Cavities Determined by using Multi-crystal Electron Diffraction2019In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, no 37, p. 13080-13086Article in journal (Refereed)
    Abstract [en]

    The high-silica zeolite SSZ-27 was synthesized using one of the isomers of the organic structure-directing agent that is known to produce the large-pore zeolite SSZ-26 (CON). The structure of the as-synthesized form was solved using multi-crystal electron diffraction data. Data were collected on eighteen crystals, and to obtain a high-quality and complete data set for structure refinement, hierarchical cluster analysis was employed to select the data sets most suitable for merging. The framework structure of SSZ-27 can be described as a combination of two types of cavities, one of which is shaped like a heart. The cavities are connected through shared 8-ring windows to create straight channels that are linked together in pairs to form a one-dimensional channel system. Once the framework structure was known, molecular modelling was used to find the best fitting isomer, and this, in turn, was isolated to improve the synthesis conditions for SSZ-27.

  • 89. Smolders, Simon
    et al.
    Willhammar, Tom
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Krajnc, Andraž
    Sentosun, Kadir
    Wharmby, Michael T.
    Lomachenko, Kirill A.
    Bals, Sara
    Mali, Gregor
    Roeffaers, Maarten B. J.
    De Vos, Dirk E.
    Bueken, Bart
    A Titanium(IV)-Based Metal-Organic Framework Featuring Defect-Rich Ti-O Sheets as an Oxidative Desulfurization Catalyst2019In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, no 27, p. 9160-9165Article in journal (Refereed)
    Abstract [en]

    While titanium-based metal-organic frameworks (MOFs) have been widely studied for their (photo) catalytic potential, only a few Ti-IV MOFs have been reported owing to the high reactivity of the employed titanium precursors. The synthesis of COK-47 is now presented, the first Ti carboxylate MOF based on sheets of (TiO6)-O-IV octahedra, which can be synthesized with a range of different linkers. COK-47 can be synthesized as an inherently defective nanoparticulate material, rendering it a highly efficient catalyst for the oxidation of thiophenes. Its structure was determined by continuous rotation electron diffraction and studied in depth by X-ray total scattering, EXAFS, and solid-state NMR. Furthermore, its photoactivity was investigated by electron paramagnetic resonance and demonstrated by catalytic photodegradation of rhodamine 6G.

  • 90. Su, Xiao-Jun
    et al.
    Gao, Meng
    Jiao, Lei
    Liao, Rong-Zhen
    Siegbahn, Per E. M.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cheng, Jin-Pei
    Zhang, Ming-Tian
    Electrocatalytic Water Oxidation by a Dinuclear Copper Complex in a Neutral Aqueous Solution2015In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 54, no 16, p. 4909-4914Article in journal (Refereed)
    Abstract [en]

    Electrocatalytic water oxidation using the oxidatively robust 2,7-[bis(2-pyridylmethyl)aminomethyl]-1,8-naphthyridine ligand (BPMAN)-based dinuclear copper(II) complex, [Cu-2(BPMAN)(-OH)](3+), has been investigated. This catalyst exhibits high reactivity and stability towards water oxidation in neutral aqueous solutions. DFT calculations suggest that the OO bond formation takes place by an intramolecular direct coupling mechanism rather than by a nucleophilic attack of water on the high-oxidation-state (CuO)-O-IV moiety.

  • 91.
    Suárez-Pantiga, Samuel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Colas, Kilian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Johansson, Magnus J.
    Mendoza, Abraham
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Scalable Synthesis of Piperazines Enabled by Visible-Light Irradiation and Aluminum Organometallics2015In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 54, no 47, p. 14094-14098Article in journal (Refereed)
    Abstract [en]

    The development of more active C-H oxidation catalysts has inspired a rapid, scalable, and stereoselective assembly of multifunctional piperazines through a [3+3] coupling of azomethine ylides. A combination of visible-light irradiation and aluminum organometallics is essential to promote this transformation, which introduces visible-light photochemistry of main-group organometallics and sets the basis for new and promising catalysts.

  • 92.
    Thiele, Christina M.
    et al.
    Clemens Schöpf Institut für Organische Chemie und Biochemie, Technische Universität Darmstadt, Petersenstrasse 22, 64287 Darmstadt (Germany).
    Schmidts, Volker
    Clemens Schöpf Institut für Organische Chemie und Biochemie, Technische Universität Darmstadt, Petersenstrasse 22, 64287 Darmstadt (Germany).
    Böttcher, Benjamin
    Clemens Schöpf Institut für Organische Chemie und Biochemie, Technische Universität Darmstadt, Petersenstrasse 22, 64287 Darmstadt (Germany).
    Louzao, Iria
    Clemens Schöpf Institut für Organische Chemie und Biochemie, Technische Universität Darmstadt, Petersenstrasse 22, 64287 Darmstadt (Germany). On leave from: Departamento de Química Orgánica, Facultad de Química, Universidad de Santiago de Compostela, 15782 Santiago de Compostela (Spain) .
    Berger, Robert
    Frankfurt Institute for Advanced Studies, Johann Wolfgang Goethe Universität, Ruth-Moufang-Strasse 1, 60438 Frankfurt (Germany).
    Maliniak, Arnold
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry.
    Stevensson, Baltzar
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry.
    On the Treatment of Conformational Flexibility when Using Residual Dipolar Couplings for Structure Determination2009In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 48, no 36, p. 6708-6712Article in journal (Refereed)
    Abstract [en]

    Mission possible! The motional averaging of NMR spectroscopic data complicates the determination of conformation and relative configuration in flexible organic molecules. Two alternative routes are discussed for the treatment of conformational equilibrium in a moderately flexible compound (see the superposition of the two conformers of the butyrolactone studied) when residual dipolar couplings are used.

  • 93.
    Tinnis, Fredrik
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Volkov, Alexey
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Slagbrand, Tove
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Chemoselective Reduction of Tertiary Amides under Thermal Control: Formation of either Aldehydes or Amines2016In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, no 14, p. 4562-4566Article in journal (Refereed)
    Abstract [en]

    The chemoselective reduction of amides in the presence of other more reactive reducible functional groups is a highly challenging transformation, and successful examples thereof are most valuable in synthetic organic chemistry. Only a limited number of systems have demonstrated the chemoselective reduction of amides over ketones. Until now, the aldehyde functionality has not been shown to be compatible in any catalytic reduction protocol. Described herein is a [Mo(CO)6]-catalyzed protocol with an unprecedented chemoselectivity and allows for the reduction of amides in the presence of aldehydes and imines. Furthermore, the system proved to be tunable by variation of the temperature, which enabled for either C−O or C−N bond cleavage that ultimately led to the isolation of both amines and aldehydes, respectively, in high chemical yields.

  • 94.
    Tolnai, Gergely L.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nilsson, Ulf J.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Efficient O-Functionalization of Carbohydrates with Electrophilic Reagents2016In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 55, no 37, p. 11226-11230Article in journal (Refereed)
    Abstract [en]

    Novel methodology for O-functionalization of carbohydrate derivatives has been established using bench-stable and easily prepared iodonium(III) reagents. Both electron-withdrawing and electron-donating aryl groups were introduced under ambient conditions and without precautions to exclude air or moisture. Furthermore, the approach was extended both to full arylation of cyclodextrin, and to trifluoroethylation of carbohydrate derivatives. This is the first general approach to introduce traditionally non-electrophilic groups into any of the OH groups around the sugar backbone. The methodology will be useful both in synthetic organic chemistry and biochemistry, as important functional groups can be incorporated under simple and robust reaction conditions in a fast and efficient manner.

  • 95. Tong, Lianpeng
    et al.
    Duan, Lele
    Xu, Yunhua
    Privalov, Timofei
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Licheng
    Structural Modifications of Mononuclear Ruthenium Complexes: A Combined Experimental and Theoretical Study on the Kinetics of Ruthenium-Catalyzed Water Oxidation2011In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, no 2, p. 445-449Article in journal (Refereed)
  • 96. Trillo, Paz
    et al.
    Slagbrand, Tove
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Adolfsson, Hans
    Straightforward alpha-Amino Nitrile Synthesis Through Mo(CO)(6)-Catalyzed Reductive Functionalization of Carboxamides2018In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 57, no 38, p. 12347-12351Article in journal (Refereed)
    Abstract [en]

    The selective reduction of amides into an intermediate hemiaminal catalyzed by Mo(CO)(6) together with the inexpensive and easy to handle TMDS (1,1,3,3-tetramethyldisiloxane) as reducing agent, followed by subsequent trapping of the hemiaminal with a cyanide source, allows for the straightforward synthesis of alpha-amino nitriles. The methodology presented here, displays high levels of chemoselectivity allowing for the reduction of amides in the presence of functional groups such as ketones, imines, aldehydes, and acids, which affords a simple route for the synthesis of alpha-amino nitriles with a broad scope of functionalities in high yields. Furthermore, the applicability of this methodology is demonstrated by scale up experiments and by derivatization of the target compounds into synthetically interesting products. The selective cyanation is successfully applied in late stage functionalizations of amide containing drugs and prolinol derivatives.

  • 97. Vesely, Jan
    et al.
    Ibrahem, Ismail
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Guiling
    Rios, Ramon
    Cordova, Armando
    Organocatalytic Enantioselective Aziridination of α,β-Unsaturated Aldehydes2007In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 46, p. 778-Article in journal (Refereed)
  • 98.
    Vesely, Jan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ibrahem, Ismail
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rios, Ramón
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Organocatalytic enantioselective aziridination of alpha,beta-unsaturated aldehydes2007In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 46, p. 778-781Article in journal (Refereed)
  • 99.
    Volkov, Alexey
    et al.
    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).
    Verho, Oscar
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mild Deoxygenation of Aromatic Ketones and Aldehydes over Pd/C Using Polymethylhydrosiloxane as the Reducing Agent2015In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 54, no 17, p. 5122-5126Article in journal (Refereed)
    Abstract [en]

    Herein, a practical and mild method for the deoxygenation of a wide range of benzylic aldehydes and ketones is described, which utilizes heterogeneous Pd/C as the catalyst together with the green hydride source, polymethylhydrosiloxane. The developed catalytic protocol is scalable and robust, as exemplified by the deoxygenation of ethyl vanillin, which was performed on a 30 mmol scale in an open-to-air setup using only 0.085 mol% Pd/C catalyst to furnish the corresponding deoxygenated product in 93% yield within 3 hours at room temperature. Furthermore, the Pd/C catalyst was shown to be recyclable up to 6 times without any observable decrease in efficiency and it exhibited low metal leaching under the reaction conditions.

  • 100.
    Volla, Chandra M. R.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-Catalyzed Aerobic Domino Oxidative Carbocyclization-Alkynylation of Allenynes2013In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, no 52, p. 14209-14213Article in journal (Refereed)
123 51 - 100 of 118
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