Rhodium(III)-Catalyzed Annulation of Azomethine Ylides with Alkynes via CH Activation

被引:81
作者
Chen, Yuye [1 ,2 ]
Wang, Fen [1 ]
Zhen, Wencui [1 ]
Li, Xingwei [1 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[2] Nanjing Univ Sci & Technol, Sch Environm & Biol Engn, Nanjing 210014, Peoples R China
关键词
alkynes; CH activation; cyclization; indenamines; rhodium; H BOND ACTIVATION; OXIDATIVE OLEFINATION; AROMATIC KETIMINES; INTERNAL ALKYNES; FUNCTIONALIZATION; RH; BENZAMIDES; RUTHENIUM; ARYLATION; COUPLING/CYCLIZATION;
D O I
10.1002/adsc.201200924
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The rhodium(III)-catalyzed coupling of azomethine ylides with alkynes via CH activation has been developed for the synthesis of indenamines in moderate to high yields. The coupled products can be further oxidized to indenones and derivatives.
引用
收藏
页码:353 / 359
页数:7
相关论文
共 76 条
[1]  
Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996
[2]   Ruthenium-Catalyzed Oxidative Annulation by Cleavage of C-H/N-H Bonds [J].
Ackermann, Lutz ;
Lygin, Alexander V. ;
Hofmann, Nora .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) :6379-6382
[3]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[4]   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
[5]  
Beck E.M., 2008, ANGEW CHEM INT EDIT, V120, P3046
[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]   Rh-Catalyzed Intermolecular Carbenoid Functionalization of Aromatic C-H Bonds by α-Diazomalonates [J].
Chan, Wai-Wing ;
Lo, Siu-Fung ;
Zhou, Zhongyuan ;
Yu, Wing-Yiu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13565-13568
[8]   Rh(III)-Catalyzed Oxidative Coupling of N-Aryl-2-aminopyridine with Alkynes and Alkenes [J].
Chen, Jinlei ;
Song, Guoyong ;
Pan, Cheng-Ling ;
Li, Xingwei .
ORGANIC LETTERS, 2010, 12 (23) :5426-5429
[9]  
Chen X., 2009, ANGEW CHEM, V121, P5196
[10]   Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality [J].
Chen, Xiao ;
Engle, Keary M. ;
Wang, Dong-Hui ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (28) :5094-5115