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

来源：

TETRAHEDRON | 2005年 / 61卷 / 26期

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

页码：6207 / 6217

页数：11

共 32 条

[11]

2-G

[12] Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].

Hassan, J ;

Sévignon, M ;

Gozzi, C ;

Schulz, E ;

Lemaire, M .

CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469

[13]

Herrmann WA, 2002, ANGEW CHEM INT EDIT, V41, P1290, DOI 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO

[14]

2-Y

[15] 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

[16] N-heterocyclic carbenes [J].

Herrmann, WA ;

Kocher, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (20) :2162-2187

[17] Catalytic cross-coupling reactions mediated by palladium/nucleophilic carbene systems [J].

Hillier, AC ;

Grasa, GA ;

Viciu, MS ;

Lee, HM ;

Yang, CL ;

Nolan, SP .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 653 (1-2) :69-82

[18] Macromolecular effect: Synthesis of a ferrocenylmethylphosphine-containing polymer as highly efficient ligands for room-temperature palladium(0)-catalyzed Suzuki cross-coupling reactions of aryl chlorides [J].

Hu, QS ;

Lu, Y ;

Tang, ZY ;

Yu, HB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :2856-2857

[19] Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis [J].

Kotha, S ;

Lahiri, K ;

Kashinath, D .

TETRAHEDRON, 2002, 58 (48) :9633-9695

[20] Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions [J].

Littke, AF ;

Dai, CY ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4020-4028

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