Rhodium(III)-catalyzed C-H activation and intermolecular annulation with terminal alkynes: from indoles to carbazoles

被引：78

作者：

Jia, Jinlong ^{[1
,2
]}

Shi, Jingjing ^{[1
]}

Zhou, Jie ^{[1
,3
]}

Liu, Xuelei ^{[1
]}

Song, Yanling ^{[2
]}

Xu, H. Eric ^{[1
,4
]}

Yi, Wei ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, VARI SIMM Ctr,Ctr Struct & Funct Drug Targets, Shanghai 201203, Peoples R China

[2] Shenyang Univ Chem Technol, Coll Pharmaceut & Biol Engn, Shenyang 110142, Peoples R China

[3] Sun Yat Sen Univ, Sch Chem & Chem Engn, Guangzhou 510275, Guangdong, Peoples R China

[4] Van Andel Res Inst, Program Struct Biol & Drug Discovery, Lab Struct Sci, Grand Rapids, MI 49503 USA

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 14期

关键词：

N BOND FORMATION; EFFICIENT SYNTHESIS; ALKYNYLATION; FUNCTIONALIZATION; ARENES; RH; ALKENYLATION; ALKALOIDS; HYDROGENATION; HETEROCYCLES;

D O I：

10.1039/c4cc09823d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein we disclose the first example of Rh(III)-catalyzed intermolecular annulation of indoles with terminal alkynes to give highly efficient one-pot access to privileged carbazoles. The mild reaction features moderate to good yields, exclusive regioselectivity, broad substrate scope, and excellent functional group tolerance.

引用

页码：2925 / 2928

页数：4

共 74 条

[1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].

Ackermann, Lutz .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295

[2] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[3] Rhodium(III)- and Iridium(III)-Catalyzed C7 Alkylation of Indolines with Diazo Compounds [J].

Ai, Wen ;

Yang, Xueyan ;

Wu, Yunxiang ;

Wang, Xuan ;

Li, Yuanchao ;

Yang, Yaxi ;

Zhou, Bing .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (52) :17653-17657

[4] Recent Advances in Transition-Metal-Catalyzed Functionalization of Unstrained Carbon-Carbon Bonds [J].

Chen, Feng ;

Wang, Teng ;

Jiao, Ning .

CHEMICAL REVIEWS, 2014, 114 (17) :8613-8661

[5] Direct Ortho Arylation of 9-(Pyridin-2-yl)-9H-carbazoles Bearing a Removable Directing Group via Palladium(II)-Catalyzed C-H Bond Activation [J].

Chu, Jean-Ho ;

Wu, Chung-Chiu ;

Chang, Deng-Hsiang ;

Lee, Ya-Ming ;

Wu, Ming-Jung .

ORGANOMETALLICS, 2013, 32 (01) :272-282

[6] Rhodium Catalyzed Chelation-Assisted C-H Bond Functionalization Reactions [J].

Colby, Denise A. ;

Tsai, Andy S. ;

Bergman, Robert G. ;

Ellman, Jonathan A. .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :814-825

[7] Preparation of conjugated 1,3-enynes by Rh(III)-catalysed alkynylation of alkenes via C-H activation [J].

Collins, Karl D. ;

Lied, Fabian ;

Glorius, Frank .

CHEMICAL COMMUNICATIONS, 2014, 50 (34) :4459-4461

[8] Recent advances in [2+2+2] cycloaddition reactions [J].

Dominguez, Gema ;

Perez-Castells, Javier .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3430-3444

[9] Rhodium-Catalyzed Oxidative Annulation of Sulfoximines and Alkynes as an Approach to 1,2-Benzothiazines [J].

Dong, Wanrong ;

Wang, Long ;

Parthasarathy, Kanniyappan ;

Pan, Fangfang ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (44) :11573-11576

[10] Efficient synthesis strategies by application of transition metal-catalyzed carbene/nitrene insertions into C-H bonds [J].

Egger, Julian ;

Carreira, Erick M. .

NATURAL PRODUCT REPORTS, 2014, 31 (04) :449-455

← 1 2 3 4 5 6 7 8 →