Mechanistic Considerations in the Development and Use of Azine, Diazine and Azole N-Oxides in Palladium-Catalyzed Direct Arylation

被引:120
作者
Fagnou, Keith [1 ]
机构
[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada
来源
C-H ACTIVATION | 2010年 / 292卷
基金
加拿大自然科学与工程研究理事会;
关键词
Direct arylation; Palladium; Catalysis; Azines; Azoles; H BOND ACTIVATION; CROSS-COUPLING REACTIONS; PROTON-ABSTRACTION MECHANISM; ARYL CHLORIDES; NITROGEN-HETEROCYCLES; EFFICIENT CATALYST; BROMIDES; SP(2); ACIDS; FUNCTIONALIZATION;
D O I
10.1007/128_2009_14
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Azines, diazines or thiazole N-oxides are highly reactive substrates in palladium-catalyzed direct arylation reaction. For these reactions, the results are inconsistent with an SEAr reaction pathway and may best fit with a concerted metalation-deprotonation-like (CMD) mechanism.
引用
收藏
页码:35 / 56
页数:22
相关论文
共 86 条
[1]   Catalytic arylation reactions by C-H bond activation with aryl tosylates [J].
Ackermann, L ;
Althammer, A ;
Born, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) :2619-2622
[2]   Assisted ruthenium-catalyzed C-H bond activation: Carboxylic acids as cocatalysts for generally applicable direct arylations in apolar solvents [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Althammer, Andreas .
ORGANIC LETTERS, 2008, 10 (11) :2299-2302
[3]  
AKITA Y, 1989, CHEM PHARM BULL, V37, P1477
[4]   SYNTHESIS AND RESOLUTION OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE - A P-N CHELATING LIGAND FOR ASYMMETRIC CATALYSIS [J].
ALCOCK, NW ;
BROWN, JM ;
HULMES, DI .
TETRAHEDRON-ASYMMETRY, 1993, 4 (04) :743-756
[5]   PALLADIUM-CATALYZED CYCLIZATION OF 2-SUBSTITUTED HALOGENOARENES BY DEHYDROHALOGENATION [J].
AMES, DE ;
OPALKO, A .
TETRAHEDRON, 1984, 40 (10) :1919-1925
[6]   SOME REACTIONS OF 3-HALOGENOCINNOLINES CATALYZED BY PALLADIUM COMPOUNDS [J].
AMES, DE ;
BULL, D .
TETRAHEDRON, 1982, 38 (03) :383-387
[7]  
AOYAGI Y, 1992, HETEROCYCLES, V33, P257
[8]   Copper-mediated C-H bond arylation of arenes with arylboronic acids [J].
Ban, Ikuya ;
Sudo, Tomoko ;
Taniguchi, Tadashi ;
Itami, Kenichiro .
ORGANIC LETTERS, 2008, 10 (16) :3607-3609
[9]   Palladium-catalysed carbomethoxyvinylation and thienylation of 5-iodo(bromo)-2,4-dimethoxypyrimidine in water [J].
Basnak, I ;
Takatori, S ;
Walker, RT .
TETRAHEDRON LETTERS, 1997, 38 (27) :4869-4872
[10]   Catalytic intermolecular ortho-arylation of phenols [J].
Bedford, RB ;
Limmert, ME .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (22) :8669-8682