One-Pot Synthesis of Indoles from Alkynes and Anilines through Palladium-Catalyzed Double C-H Activation using O2 as the oxidant

被引：6

作者：

Shi, Dunfa ^{[1
]}

Guan, Zhipeng ^{[1
]}

Yao, Xiuwen ^{[1
]}

Shi, Wei ^{[1
]}

Chen, Hao ^{[1
]}

机构：

[1] Huazhong Agr Univ, Dept Chem, Coll Sci, Wuhan 430070, Peoples R China

来源：

CHEMISTRYSELECT | 2016年 / 1卷 / 01期

基金：

中国国家自然科学基金;

关键词：

Indole synthesis; cyanoalkynes; C-H activation; Palladium-catalyzed; EFFICIENT;

D O I：

10.1002/slct.201500015

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple and efficient Pd-catalyzed tandem procedure for the synthesis of beta-cyanoindoles was achieved. Unactivated anilines and cyanoalkynes were employed as the starting materials to go through nucleophilic additions to form the N-aryl enamine intermediate, and then followed by Pd-catalyzed double C-H activation to yield the product in one pot. Moderate to good yields were achieved for 19 examples. LiBr was used as the additive to promote the process. Oxygen was used as the sole oxidant, thus high atom efficiency could be achieved.

引用

页码：119 / 121

页数：3

共 18 条

[11] Rhodium(III)-Catalyzed Arene and Alkene C-H Bond Functionalization Leading to Indoles and Pyrroles [J].

Stuart, David R. ;

Alsabeh, Pamela ;

Kuhn, Michelle ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (51) :18326-18339

[12] Indole Synthesis via Rhodium Catalyzed Oxidative Coupling of Acetanilides and Internal Alkynes [J].

Stuart, David R. ;

Bertrand-Laperle, Megan ;

Burgess, Kevin M. N. ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (49) :16474-+

[13] Indole synthesis: a review and proposed classification [J].

Taber, Douglass F. ;

Tirunahari, Pavan K. .

TETRAHEDRON, 2011, 67 (38) :7195-7210

[14] Recent advances in indole syntheses: New routes for a classic target [J].

Vicente, Ruben .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (19) :6469-6480

[15] Traceless Directing Strategy: Efficient Synthesis of N-Alkyl Indoles via Redox-Neutral C-H Activation [J].

Wang, Chengming ;

Huang, Yong .

ORGANIC LETTERS, 2013, 15 (20) :5294-5297

[16] Palladium-catalyzed oxidative cyclization of N-aryl enamines:: From anilines to indoles [J].

Wuertz, Sebastian ;

Rakshit, Souvik ;

Neumann, Julia J. ;

Droege, Thomas ;

Glorius, Frank .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (38) :7230-7233

[17] Rh-Catalyzed oxidative C-H activation/annulation: converting anilines to indoles using molecular oxygen as the sole oxidant [J].

Zhang, Guoying ;

Yu, Hui ;

Qin, Guiping ;

Huang, Hanmin .

CHEMICAL COMMUNICATIONS, 2014, 50 (33) :4331-4334

[18] Synthesis of indoles via palladium-catalyzed C-H activation of N-aryl amides followed by coupling with alkynes [J].

Zhou, Feng ;

Han, Xiuling ;

Lu, Xiyan .

TETRAHEDRON LETTERS, 2011, 52 (36) :4681-4685

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