Fernandes, Antony E.
[Massachusetts Institute of Technology (USA)]
Riant, Olivier
[UCL]
Jensen, Klavs F.
[Massachusetts Institute of Technology (USA)]
Jonas, Alain M.
[UCL]
We describe a simple and general method for the preparation and molecular engineering of supported trifunctional catalysts and their application in the representative Cu/TEMPO/NMI-catalyzed aerobic oxidation of benzyl alcohol. The methodology allows in one single step to immobilize, with precise control of surface composition, both pyta, CuI, TEMPO, and NMI sites on azide-functionalized silica particles. To optimize the performance of the heterogeneous trifunctional catalysts, synergistic interactions are finely engineered through modulating the degree of freedom of the imidazole site as well as tuning the relative surface composition,leading to catalysts with an activity significantly superior to the corresponding homogeneous catalytic system.
- Notestein Justin M., Katz Alexander, Enhancing Heterogeneous Catalysis through Cooperative Hybrid Organic–Inorganic Interfaces, 10.1002/chem.200501152
- Felpin François-Xavier, Fouquet Eric, Heterogeneous Multifunctional Catalysts for Tandem Processes: An Approach toward Sustainability, 10.1002/cssc.200800110
- Lee Jeong-Kyu, Kung Mayfair C., Kung Harold H., Cooperative Catalysis: A New Development in Heterogeneous Catalysis, 10.1007/s11244-008-9087-y
- Motokura Ken, Tada Mizuki, Iwasawa Yasuhiro, Acid-Base Bifunctional Catalytic Surfaces for Nucleophilic Addition Reactions, 10.1002/asia.200800126
- Margelefsky Eric L., Zeidan Ryan K., Davis Mark E., Cooperative catalysis by silica-supported organic functional groups, 10.1039/b710334b
- Shylesh Sankaranarayanapillai, Thiel Werner R., Bifunctional Acid-Base Cooperativity in Heterogeneous Catalytic Reactions: Advances in Silica Supported Organic Functional Groups, 10.1002/cctc.201000353
- Yu Chenguang, He Jing, Synergic catalytic effects in confined spaces, 10.1039/c2cc31585h
- Brunelli Nicholas A., Jones Christopher W., Tuning acid–base cooperativity to create next generation silica-supported organocatalysts, 10.1016/j.jcat.2013.05.022
- Díaz Urbano, Brunel Daniel, Corma Avelino, Catalysis using multifunctional organosiliceous hybrid materials, 10.1039/c2cs35385g
- Climent Maria J., Corma Avelino, Iborra Sara, Sabater Maria J., Heterogeneous Catalysis for Tandem Reactions, 10.1021/cs401052k
- Motokura Ken, Multifunctional Solid Surfaces for Enhanced Catalysis, 10.1002/cctc.201402585
- Shiju N. Raveendran, Alberts Albert H., Khalid Syed, Brown David R., Rothenberg Gadi, Mesoporous Silica with Site-Isolated Amine and Phosphotungstic Acid Groups: A Solid Catalyst with Tunable Antagonistic Functions for One-Pot Tandem Reactions, 10.1002/ange.201101449
- Shiju N. Raveendran, Alberts Albert H., Khalid Syed, Brown David R., Rothenberg Gadi, Mesoporous Silica with Site-Isolated Amine and Phosphotungstic Acid Groups: A Solid Catalyst with Tunable Antagonistic Functions for One-Pot Tandem Reactions, 10.1002/anie.201101449
- Lohr Tracy L., Marks Tobin J., Orthogonal tandem catalysis, 10.1038/nchem.2262
- Wheeldon Ian, Minteer Shelley D., Banta Scott, Barton Scott Calabrese, Atanassov Plamen, Sigman Matthew, Substrate channelling as an approach to cascade reactions, 10.1038/nchem.2459
- Huh Seong, Chen Hung-Ting, Wiench Jerzy W., Pruski Marek, Lin Victor S.-Y., Cooperative Catalysis by General Acid and Base Bifunctionalized Mesoporous Silica Nanospheres, 10.1002/ange.200462424
- Huh Seong, Chen Hung-Ting, Wiench Jerzy W., Pruski Marek, Lin Victor S.-Y., Cooperative Catalysis by General Acid and Base Bifunctionalized Mesoporous Silica Nanospheres, 10.1002/anie.200462424
- Zeidan Ryan K., Hwang Son-Jong, Davis Mark E., Multifunctional Heterogeneous Catalysts: SBA-15-Containing Primary Amines and Sulfonic Acids, 10.1002/ange.200602243
- Zeidan Ryan K., Hwang Son-Jong, Davis Mark E., Multifunctional Heterogeneous Catalysts: SBA-15-Containing Primary Amines and Sulfonic Acids, 10.1002/anie.200602243
- Sharma Krishna K., Asefa Tewodros, Efficient Bifunctional Nanocatalysts by Simple Postgrafting of Spatially Isolated Catalytic Groups on Mesoporous Materials, 10.1002/ange.200604570
- Sharma Krishna K., Asefa Tewodros, Efficient Bifunctional Nanocatalysts by Simple Postgrafting of Spatially Isolated Catalytic Groups on Mesoporous Materials, 10.1002/anie.200604570
- Motokura Ken, Tada Mizuki, Iwasawa Yasuhiro, Cooperative Catalysis of Primary and Tertiary Amines Immobilized on Oxide Surfaces for One-Pot CC Bond Forming Reactions, 10.1002/ange.200802515
- Motokura Ken, Tada Mizuki, Iwasawa Yasuhiro, Cooperative Catalysis of Primary and Tertiary Amines Immobilized on Oxide Surfaces for One-Pot CC Bond Forming Reactions, 10.1002/anie.200802515
- Sharma Krishna K., Buckley Robert P., Asefa Tewodros, Optimizing Acid−Base Bifunctional Mesoporous Catalysts for the Henry Reaction: Effects of the Surface Density and Site Isolation of Functional Groups, 10.1021/la8030107
- Shylesh Sankaranarayanapillai, Wagner Alex, Seifert Andreas, Ernst Stefan, Thiel Werner R., Cooperative Acid-Base Effects with Functionalized Mesoporous Silica Nanoparticles: Applications in Carbon-Carbon Bond-Formation Reactions, 10.1002/chem.200900851
- Shylesh Sankaranarayanapillai, Wagener Alex, Seifert Andreas, Ernst Stefan, Thiel Werner R., Mesoporöse Organokieselgele mit sauren Wänden und basischen Gruppen im Poreninneren: ein Ansatz für die kooperative Katalyse, 10.1002/ange.200903985
- Shylesh Sankaranarayanapillai, Wagener Alex, Seifert Andreas, Ernst Stefan, Thiel Werner R., Mesoporous Organosilicas with Acidic Frameworks and Basic Sites in the Pores: An Approach to Cooperative Catalytic Reactions, 10.1002/anie.200903985
- Sharma Krishna K., Biradar Ankush V., Das Sayantani, Asefa Tewodros, Bifunctional Mesoporous Silica Catalyst for C-C Bond Forming Tandem Reactions, 10.1002/ejic.201001332
- Noda Hiroto, Motokura Ken, Miyaji Akimitsu, Baba Toshihide, Heterogeneous Synergistic Catalysis by a Palladium Complex and an Amine on a Silica Surface for Acceleration of the Tsuji-Trost Reaction, 10.1002/ange.201203066
- Noda Hiroto, Motokura Ken, Miyaji Akimitsu, Baba Toshihide, Heterogeneous Synergistic Catalysis by a Palladium Complex and an Amine on a Silica Surface for Acceleration of the Tsuji-Trost Reaction, 10.1002/anie.201203066
- Noda Hiroto, Motokura Ken, Miyaji Akimitsu, Baba Toshihide, Efficient Allylation of Nucleophiles Catalyzed by a Bifunctional Heterogeneous Palladium Complex-Tertiary Amine System, 10.1002/adsc.201300063
- Motokura Ken, Ito Yasuhiro, Noda Hiroto, Miyaji Akimitsu, Yamaguchi Sho, Baba Toshihide, Surface Functionalization for Synergistic Catalysis: Silica-Alumina-Supported Cationic Indium and Organic Base for Cyanoethoxycarbonylation, 10.1002/cplu.201402004
- Noda Hiroto, Motokura Ken, Chun Wang-Jae, Miyaji Akimitsu, Yamaguchi Sho, Baba Toshihide, Heterogeneous double-activation catalysis: Rh complex and tertiary amine on the same solid surface for the 1,4-addition reaction of aryl- and alkylboronic acids, 10.1039/c5cy00133a
- Zhao Qingshan, Zhu Yuanzhi, Sun Zhen, Li Yang, Zhang Guoliang, Zhang Fengbao, Fan Xiaobin, Combining palladium complex and organic amine on graphene oxide for promoted Tsuji–Trost allylation, 10.1039/c4ta05205f
- Huh Seong, Chen Hung-Ting, Wiench Jerzy W., Pruski Marek, Lin Victor S.-Y., Controlling the Selectivity of Competitive Nitroaldol Condensation by Using a Bifunctionalized Mesoporous Silica Nanosphere-Based Catalytic System, 10.1021/ja0398161
- Margelefsky Eric L., Bendjériou Anissa, Zeidan Ryan K., Dufaud Véronique, Davis Mark E., Nanoscale Organization of Thiol and Arylsulfonic Acid on Silica Leads to a Highly Active and Selective Bifunctional, Heterogeneous Catalyst, 10.1021/ja804082m
- Paluti Christy C., Gawalt Ellen S., Immobilized aza-bis(oxazoline) copper catalysts on alkanethiol self-assembled monolayers on gold: Selectivity dependence on surface electronic environments, 10.1016/j.jcat.2010.07.027
- Xiao Wei, Jin Ronghua, Cheng Tanyu, Xia Daquan, Yao Hui, Gao Fei, Deng Boxin, Liu Guohua, A bifunctionalized organic–inorganic hybrid silica: synergistic effect enhances enantioselectivity, 10.1039/c2cc36350j
- Dickschat Arne T., Behrends Frederik, Surmiak Sabrina, Weiß Mark, Eckert Hellmut, Studer Armido, Bifunctional mesoporous silica nanoparticles as cooperative catalysts for the Tsuji–Trost reaction – tuning the reactivity of silica nanoparticles, 10.1039/c3cc00235g
- Deiana Luca, Ghisu Lorenza, Afewerki Samson, Verho Oscar, Johnston Eric V., Hedin Niklas, Bacsik Zoltan, Córdova Armando, Enantioselective Heterogeneous Synergistic Catalysis for Asymmetric Cascade Transformations, 10.1002/adsc.201400291
- Puglisi Alessandra, Annunziata Rita, Benaglia Maurizio, Cozzi Franco, Gervasini Antonella, Bertacche Vittorio, Sala Maria Chiara, Hybrid Inorganic-Organic Materials Carrying Tertiary Amine and Thiourea Residues Tethered on Mesoporous Silica Nanoparticles: Synthesis, Characterization, and Co-Operative Catalysis, 10.1002/adsc.200800635
- Tsai Chih-Hsiang, Chen Hung-Ting, Althaus Stacey M., Mao Kanmi, Kobayashi Takeshi, Pruski Marek, Lin Victor S.-Y., Rational Catalyst Design: A Multifunctional Mesoporous Silica Catalyst for Shifting the Reaction Equilibrium by Removal of Byproduct, 10.1021/cs200222t
- Brunelli Nicholas A., Venkatasubbaiah Krishnan, Jones Christopher W., Cooperative Catalysis with Acid–Base Bifunctional Mesoporous Silica: Impact of Grafting and Co-condensation Synthesis Methods on Material Structure and Catalytic Properties, 10.1021/cm300753z
- Brunelli Nicholas A., Didas Stephanie A., Venkatasubbaiah Krishnan, Jones Christopher W., Tuning Cooperativity by Controlling the Linker Length of Silica-Supported Amines in Catalysis and CO2 Capture, 10.1021/ja305601g
- Shylesh, ChemCatChem, 6, 1283 (2014)
- Dickschat Arne T., Behrends Frederik, Bühner Martin, Ren Jinjun, Weiß Mark, Eckert Hellmut, Studer Armido, Preparation of Bifunctional Mesoporous Silica Nanoparticles by Orthogonal Click Reactions and Their Application in Cooperative Catalysis, 10.1002/chem.201200499
- Studer Armido, Dickschat Arne, Surmiak Sabrina, Pd Immobilized in Mesoporous Silica Particles as Recyclable Catalysts for Suzuki-Miyaura Coupling: Cooperative Effects Exerted by Co-Immobilized Amine Functionalities, 10.1055/s-0033-1339183
- Hoover Jessica M, Steves Janelle E, Stahl Shannon S, Copper(I)/TEMPO-catalyzed aerobic oxidation of primary alcohols to aldehydes with ambient air, 10.1038/nprot.2012.057
- Ryland Bradford L., Stahl Shannon S., Praktische aerobe Oxidationen von Alkoholen und Aminen mit dem homogenen Kupfer/TEMPO- und verwandten Katalysatorsystemen, 10.1002/ange.201403110
- Ryland Bradford L., Stahl Shannon S., Practical Aerobic Oxidations of Alcohols and Amines with Homogeneous Copper/TEMPO and Related Catalyst Systems, 10.1002/anie.201403110
- Rabeah Jabor, Bentrup Ursula, Stößer Reinhard, Brückner Angelika, Selective Alcohol Oxidation by a Copper TEMPO Catalyst: Mechanistic Insights by Simultaneously Coupled Operando EPR/UV-Vis/ATR-IR Spectroscopy, 10.1002/ange.201504813
- Rabeah Jabor, Bentrup Ursula, Stößer Reinhard, Brückner Angelika, Selective Alcohol Oxidation by a Copper TEMPO Catalyst: Mechanistic Insights by Simultaneously Coupled Operando EPR/UV-Vis/ATR-IR Spectroscopy, 10.1002/anie.201504813
- Fernandes Antony E., Riant Olivier, Jonas Alain M., Jensen Klavs F., One “Click” to controlled bifunctional supported catalysts for the Cu/TEMPO-catalyzed aerobic oxidation of alcohols, 10.1039/c6ra05026c
- Fernandes Antony E., Jonas Alain M., Riant Olivier, Application of CuAAC for the covalent immobilization of homogeneous catalysts, 10.1016/j.tet.2013.12.034
- Hoover Jessica M., Stahl Shannon S., Highly Practical Copper(I)/TEMPO Catalyst System for Chemoselective Aerobic Oxidation of Primary Alcohols, 10.1021/ja206230h
- Hoover Jessica M., Ryland Bradford L., Stahl Shannon S., Mechanism of Copper(I)/TEMPO-Catalyzed Aerobic Alcohol Oxidation, 10.1021/ja3117203
- Hoover Jessica M., Ryland Bradford L., Stahl Shannon S., Copper/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Mechanistic Assessment of Different Catalyst Systems, 10.1021/cs400689a
- Zhang Guofu, Wang Yong, Wen Xin, Ding Chengrong, Li Ying, Dual-functional click-triazole: a metal chelator and immobilization linker for the construction of a heterogeneous palladium catalyst and its application for the aerobic oxidation of alcohols, 10.1039/c2cc18023e
- Wang Dong, Denux Dominique, Ruiz Jaime, Astruc Didier, The Clicked Pyridyl-Triazole Ligand: From Homogeneous to Robust, Recyclable Heterogeneous Mono- and Polymetallic Palladium Catalysts for Efficient Suzuki-Miyaura, Sonogashira, and Heck Reactions, 10.1002/adsc.201200619
- Gheorghe Alexandru, Matsuno Ai, Reiser Oliver, Expedient Immobilization of TEMPO by Copper-Catalyzed Azide-Alkyne [3+2]-Cycloaddition onto Polystyrene Resin, 10.1002/adsc.200606043
- Ryland Bradford L., McCann Scott D., Brunold Thomas C., Stahl Shannon S., Mechanism of Alcohol Oxidation Mediated by Copper(II) and Nitroxyl Radicals, 10.1021/ja5070137
- Crowley James D., Bandeen Pauline H., Hanton Lyall R., A one pot multi-component CuAAC “click” approach to bidentate and tridentate pyridyl-1,2,3-triazole ligands: Synthesis, X-ray structures and copper(II) and silver(I) complexes, 10.1016/j.poly.2009.06.010
Bibliographic reference |
Fernandes, Antony E. ; Riant, Olivier ; Jensen, Klavs F. ; Jonas, Alain M.. Molecular Engineering of trifunctional supported catalysts for the aerobic oxidation of alcohols. In: Angewandte Chemie (International Edition), Vol. 55, p. 11044-11048 (2016) |
Permanent URL |
http://hdl.handle.net/2078.1/181260 |