Imidazo[1,5-a]pyridine-3-ylidenes -: pyridine derived N-heterocyclic carbene ligands

被引:165
作者
Burstein, C [1 ]
Lehmann, CW [1 ]
Glorius, F [1 ]
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
ligand design; N-heterocyclic carbene; Suzuki-Miyaura cross-coupling;
D O I
10.1016/j.tet.2005.03.115
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ready synthesis of differently substituted 2H-imidazo[1,5-a]pyridin-4-ium bromides is reported. These salts are precursors for a new class of N-heterocyclic carbene ligands. As a consequence of their bicyclic geometry, these ligands are capable of influencing the coordination sphere of a carbene bound metal. The usefulness of these ligands was demonstrated in the palladium-catalyzed Suzuki-Miyaura cross-coupling, of sterically hindered aryl chlorides. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6207 / 6217
页数:11
相关论文
共 32 条
[1]   Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis [J].
Altenhoff, G ;
Goddard, R ;
Lehmann, CW ;
Glorius, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15195-15201
[2]   An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature [J].
Altenhoff, G ;
Goddard, R ;
Lehmann, CW ;
Glorius, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3690-3693
[3]  
[Anonymous], 2004, METAL CATALYZED CROS
[4]   The quest for stable carbenes [J].
Arduengo, AJ ;
Krafczyk, R .
CHEMIE IN UNSERER ZEIT, 1998, 32 (01) :6-14
[5]   Stable carbenes [J].
Bourissou, D ;
Guerret, O ;
Gabbaï, FP ;
Bertrand, G .
CHEMICAL REVIEWS, 2000, 100 (01) :39-91
[6]   The first applications of carbene ligands in cross-couplings of alkyl electrophiles: Sonogashira reactions of unactivated alkyl bromides and iodides [J].
Eckhardt, M ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (45) :13642-13643
[7]  
ENDERS D, 2001, J ORGANOMET CHEM, V70, P617
[8]   Chiral olefin Ligands - New "Spectators" in asymmetric catalysis [J].
Glorius, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3364-3366
[9]   Oxazolines as chiral building blocks for imidazolium salts and N-heterocyclic carbene ligands [J].
Glorius, F ;
Altenhoff, G ;
Goddard, R ;
Lehmann, C .
CHEMICAL COMMUNICATIONS, 2002, (22) :2704-+
[10]  
Gstöttmayr CWK, 2002, ANGEW CHEM INT EDIT, V41, P1363, DOI 10.1002/1521-3773(20020415)41:8<1363::AID-ANIE1363>3.0.CO