A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides

被引:485
作者
Campeau, LC [1 ]
Rousseaux, S [1 ]
Fagnou, K [1 ]
机构
[1] Univ Ottawa, Dept Chem, Ctr Catalysis Res & Innovat, Ottawa, ON K1N 6N5, Canada
关键词
D O I
10.1021/ja056800x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Direct arylation reactions of pyridine N-oxides occur in excellent yield with complete selectivity for the 2-position with a wide range of aryl bromides. This reactivity permits the use of inexpensive, commercially available, and bench-stable pyridine N-oxides as replacements for problematic 2-metallapyridines in palladium-catalyzed cross-coupling reactions. Copyright © 2005 American Chemical Society.
引用
收藏
页码:18020 / 18021
页数:2
相关论文
共 30 条
[1]   ANALYSIS OF DIFFERENTIAL SCANNING CALORIMETRIC DATA FOR REACTIVE CHEMICALS [J].
ANDO, T ;
FUJIMOTO, Y ;
MORISAKI, S .
JOURNAL OF HAZARDOUS MATERIALS, 1991, 28 (03) :251-280
[2]  
Aoyagi Y, 1997, SYNTHESIS-STUTTGART, P891
[3]  
BALICKI R, 1989, SYNTHESIS-STUTTGART, P645
[4]   Biaryl synthesis via direct arylation: Establishment of an efficient catalyst for intramolecular processes [J].
Campeau, LC ;
Parisien, M ;
Leblanc, M ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9186-9187
[5]  
CAMPEAU LC, 2005, IN PRESS J AM CHEM S
[6]  
DAUGULIS O, 2005, ANGEW CHEM INT EDIT, V44, P2
[7]   A general [3+2+1] annulation strategy for the preparation of pyridine N-oxides [J].
Davies, IW ;
Marcoux, JF ;
Reider, PJ .
ORGANIC LETTERS, 2001, 3 (02) :209-211
[8]  
Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222
[9]   Exploiting the versatile assembly of arylpyridine fluorophores for wavelength tuning and SAR [J].
Fang, AG ;
Mello, JV ;
Finney, NS .
ORGANIC LETTERS, 2003, 5 (07) :967-970
[10]   RETRACTED: Site-specific phenylation of pyridine catalyzed by phosphido-bridged ruthenium dimer complexes: A prototype for C-H arylation of electron-deficient heteroarenes (Retracted Article. See vol 128, pg 3102, 2006) [J].
Godula, K ;
Sezen, B ;
Sames, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (11) :3648-3649