New N-Heterocyclic Carbene Palladium Complex/Ionic Liquid Matrix Immobilized on Silica: Application as Recoverable Catalyst for the Heck Reaction

作者: Babak Karimi , Dieter Enders

DOI: 10.1021/OL060129Z

关键词: Matrix (chemical analysis)Thermal stabilityIonic liquidPolymer chemistryHeck reactionCovalent bondChemistryCarbeneInorganic chemistryCatalysisPalladium

摘要: A new concept of simultaneous covalent anchoring a N-heterocyclic carbene palladium/ionic liquid matrix on the silica surface and application resulting catalyst in Heck reaction variety different haloarenes is described. The shows high thermal stability (up to 280 °C) could be recovered reused for four cycles, giving total TON ≅ 36 600. Furthermore, TEM coupled with EDX analysis indicate formation Pd nanoparticles within immobilized IL layer.

参考文章(27)
Jürgen Schwarz, Volker P. W. Böhm, Michael G. Gardiner, Manja Grosche, Wolfgang A. Herrmann, Wolfgang Hieringer, Gabriele Raudaschl-Sieber, Polymer‐Supported Carbene Complexes of Palladium: Well‐Defined, Air‐Stable, Recyclable Catalysts for the Heck Reaction Chemistry: A European Journal. ,vol. 6, pp. 1773- 1780 ,(2000) , 10.1002/(SICI)1521-3765(20000515)6:10<1773::AID-CHEM1773>3.0.CO;2-P
Cathleen M. Crudden, Mutyala Sateesh, Roxanne Lewis, Mercaptopropyl-Modified Mesoporous Silica:  A Remarkable Support for the Preparation of a Reusable, Heterogeneous Palladium Catalyst for Coupling Reactions Journal of the American Chemical Society. ,vol. 127, pp. 10045- 10050 ,(2005) , 10.1021/JA0430954
Irina P. Beletskaya, Andrei V. Cheprakov, The Heck Reaction as a Sharpening Stone of Palladium Catalysis Chemical Reviews. ,vol. 100, pp. 3009- 3066 ,(2000) , 10.1021/CR9903048
Merritt B. Andrus, Chun Song, Jiuqing Zhang, Palladium-imidazolium carbene catalyzed Mizoroki-Heck coupling with aryl diazonium ions. Organic Letters. ,vol. 4, pp. 2079- 2082 ,(2002) , 10.1021/OL025961S
Costa Metallinos, Fred B. Barrett, Jennifer L. Chaytor, Mary E. A. Heska, A benzimidazole-based N-heterocyclic carbene derived from 1,10-phenanthroline. Organic Letters. ,vol. 6, pp. 3641- 3644 ,(2004) , 10.1021/OL048393K
Christian P. Mehnert, Raymond A. Cook, Nicholas C. Dispenziere, Mobae Afeworki, Supported ionic liquid catalysis--a new concept for homogeneous hydroformylation catalysis. Journal of the American Chemical Society. ,vol. 124, pp. 12932- 12933 ,(2002) , 10.1021/JA0279242
Jennifer A. Loch, Martin Albrecht, Eduardo Peris, José Mata, Jack W. Faller, Robert H. Crabtree, Palladium Complexes with Tridentate Pincer Bis-Carbene Ligands as Efficient Catalysts for C−C Coupling Organometallics. ,vol. 21, pp. 700- 706 ,(2002) , 10.1021/OM010852N
Nidhi Jain, Anil Kumar, Sushma Chauhan, S.M.S. Chauhan, Chemical and biochemical transformations in ionic liquids Tetrahedron. ,vol. 61, pp. 1015- 1060 ,(2005) , 10.1016/J.TET.2004.10.070