New N-heterocyclic carbene palladium complex/ionic liquid matrix immobilized on silica: Application as recoverable catalyst for the Heck reaction

被引：275
作者：
Karimi, B
Enders, D
机构：
[1] Inst Adv Studies Basic Sci, Dept Chem, Zanjan, Iran
[2] Inst Fundamental Res, Tehran, Iran
[3] Univ Aachen, Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 06期
关键词：
D O I：
10.1021/ol060129z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new concept of simultaneous covalent anchoring of a N-heterocyclic carbene palladium/ionic liquid matrix on the silica surface and the application of the resulting catalyst in the Heck reaction of a variety of different haloarenes is described. The catalyst shows high thermal stability (up to 280 degrees C) and could be recovered and reused for four reaction cycles, giving a total TON congruent to 36600. Furthermore, TEM coupled with EDX analysis indicate the formation of Pd nanoparticles within the immobilized IL layer.
引用
收藏
页码：1237 / 1240
页数：4
相关论文
共 42 条
[1]   Palladium-imidazolium carbene catalyzed Mizoroki-Heck coupling with aryl diazonium ions [J].
Andrus, MB ;
Song, C ;
Zhang, JQ .
ORGANIC LETTERS, 2002, 4 (12) :2079-2082
[2]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[3]  
Brase S, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P99
[4]   Preparation of polymer-supported palladium/N-heterocyclic carbene complex for Suzuki cross-coupling reactions [J].
Byun, JW ;
Lee, YS .
TETRAHEDRON LETTERS, 2004, 45 (09) :1837-1840
[5]   RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION [J].
CABRI, W ;
CANDIANI, I .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) :2-7
[6]   The role of Pd nanoparticles in ionic liquid in the Heck reaction [J].
Cassol, CC ;
Umpierre, AP ;
Machado, G ;
Wolke, SI ;
Dupont, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) :3298-3299
[7]   Layered double hydroxide supported nanopalladium catalyst for Heck-, Suzuki-, Sonogashira-, and Stille-type coupling reactions of chloroarenes [J].
Choudary, BM ;
Madhi, S ;
Chowdari, NS ;
Kantam, ML ;
Sreedhar, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (47) :14127-14136
[8]   Mercaptopropyl-modified mesoporous silica: A remarkable support for the preparation of a reusable, heterogeneous palladium catalyst for coupling reactions [J].
Crudden, CM ;
Sateesh, M ;
Lewis, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) :10045-10050
[9]   1-(2-iodophenyl)-1H-tetrazole as a ligand for Pd(II) catalyzed Heck reaction [J].
Gupta, AK ;
Song, CH ;
Oh, CH .
TETRAHEDRON LETTERS, 2004, 45 (21) :4113-4116
[10]   METAL-COMPLEXES OF N-HETEROCYCLIC CARBENES - A NEW STRUCTURAL PRINCIPLE FOR CATALYSTS IN HOMOGENEOUS CATALYSIS [J].
HERRMANN, WA ;
ELISON, M ;
FISCHER, J ;
KOCHER, C ;
ARTUS, GRJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (21) :2371-2374
12345