Electronic nature of N-heterocyclic carbene ligands: Effect on the Suzuki reaction

被引：174

作者：

Hadei, N ^{[1
]}

Kantchev, EAB ^{[1
]}

O'Brien, CJ ^{[1
]}

Organ, MG ^{[1
]}

机构：

[1] York Univ, Dept Chem, Toronto, ON M3J 1P3, Canada

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 10期

关键词：

D O I：

10.1021/ol050471w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Suzuki reactions of aryl chlorides and arylboronic acids with a range of electronically different N-heterocyclic carbene ligands derived from N,N-diadamantylbenzimidazolium salts are reported. Results indicate that an electron-rich NHC ligand enhances the rate of oxidative addition. However, reductive elimination is unchanged by the electronic nature of the supporting ligand and is primarily affected by the steric environment.

引用

页码：1991 / 1994

页数：4

共 29 条

[1] Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis
Altenhoff, G
Goddard, R
Lehmann, CW
Glorius, F
[J]. 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
Altenhoff, G
Goddard, R
Lehmann, CW
Glorius, F
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) : 3690 - 3693
[3] Suzuki-Miyaura cross-coupling of aryl and alkyl halides using palladium/imidazolium salt protocols
Arentsen, K
Caddick, S
Geoffrey, F
Cloke, N
Herring, AP
Hitchcock, PB
[J]. TETRAHEDRON LETTERS, 2004, 45 (17) : 3511 - 3515
[4] AUDREU MG, 2000, CHEM COMMUN, P2475
[5] Efficient catalyst for the Suzuki-Miyaura coupling of potassium aryl trifluoroborates with aryl chlorides
Barder, TE
Buchwald, SL
[J]. ORGANIC LETTERS, 2004, 6 (16) : 2649 - 2652
[6] Carbamoyl-substituted N-heterocyclic carbene complexes of palladium(II):: Application to Sonogashira cross-coupling reactions
Batey, RA
Shen, M
Lough, AJ
[J]. ORGANIC LETTERS, 2002, 4 (09) : 1411 - 1414
[7] Monoligated palladium species as catalysts in cross-coupling reactions
Christmann, U
Vilar, R
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (03) : 366 - 374
[8] Gstöttmayr CWK, 2002, ANGEW CHEM INT EDIT, V41, P1363, DOI 10.1002/1521-3773(20020415)41:8<1363::AID-ANIE1363>3.0.CO
[9] 2-G
[10] Herrmann WA, 2002, ANGEW CHEM INT EDIT, V41, P1290, DOI 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO

← 1 2 3 →