Pd-Catalyzed C-H Bond Functionalization on the Indole and Pyrrole Nucleus

被引:220
作者
Beck, Elizabeth M. [1 ]
Gaunt, Matthew J. [1 ]
机构
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
来源
C-H ACTIVATION | 2010年 / 292卷
基金
英国工程与自然科学研究理事会;
关键词
Palladium; Indole; Pyrrole; C-H activation; DIRECT ARYLATION; REGIOSELECTIVE SYNTHESIS; COUPLING REACTIONS; ROOM-TEMPERATURE; HECK REACTION; PALLADIUM(II); OLEFINS; ALKENYLATION; HETEROCYCLES; ACTIVATION;
D O I
10.1007/128_2009_15
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This review details recent developments in the Pd-catalyzed C-H bond arylation and alkenylation of indoles and pyrroles, aromatic heterocycles that are frequently displayed in natural products and medicinal agents.
引用
收藏
页码:85 / 121
页数:37
相关论文
共 84 条
[1]   Regioselectivity on the palladium-catalyzed intramolecular cyclization of indole derivatives [J].
Abbiati, G ;
Beccalli, EM ;
Broggini, G ;
Zoni, C .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (20) :7625-7628
[2]  
AKITA Y, 1989, CHEM PHARM BULL, V37, P1477
[3]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[4]   Short, enantioselective total synthesis of okaramine N [J].
Baran, PS ;
Guerrero, CA ;
Corey, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (19) :5628-5629
[5]   A short synthetic route to (+)-austamide, (+)-deoxyisoaustamide, and (+)-hydratoaustamide from a common precursor by a novel palladium-mediated indole→dihydroindoloazocine cyclization [J].
Baran, PS ;
Corey, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7904-7905
[6]   Synthesis of rhazinicine by a metal-catalyzed C-H bond functionalization strategy [J].
Beck, Elizabeth M. ;
Hatley, Richard ;
Gaunt, Matthew J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (16) :3004-3007
[7]   Mild aerobic oxidative palladium (II) catalyzed C-H bond functionalization: Regioselective and switchable C-H alkenylation and annulation of pyrroles [J].
Beck, EM ;
Grimster, NP ;
Hatley, R ;
Gaunt, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2528-2529
[8]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[9]   Concise synthesis of (±)-rhazinilam through direct coupling [J].
Bowie, AL ;
Hughes, CC ;
Trauner, D .
ORGANIC LETTERS, 2005, 7 (23) :5207-5209
[10]   Twofold C-H functionalization:: Palladium-catalyzed ortho arylation of anilides [J].
Brasche, Gordon ;
Garcia-Fortanet, Jorge ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2008, 10 (11) :2207-2210