Electrocatalytic intramolecular oxidative annulation of N-aryl enamines into substituted indoles mediated by iodides

被引：122

作者：

Tang, Shan ^{[1
]}

Gao, Xinlong ^{[1
]}

Lei, Aiwen ^{[1
,2
]}

机构：

[1] Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Studies, Wuhan 430072, Hubei, Peoples R China

[2] Jiangxi Normal Univ, Natl Res Ctr Carbohydrate Synth, Nanchang 330022, Jiangxi, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 23期

基金：

中国国家自然科学基金;

关键词：

H FUNCTIONALIZATION SYNTHESIS; CROSS-COUPLING REACTION; C BOND FORMATION; ELECTROCHEMICAL SYNTHESIS; ORGANIC ELECTROSYNTHESIS; CONSTRUCTION; CYCLIZATION; INDOLIZINES; CATALYSIS; EFFICIENT;

D O I：

10.1039/c7cc00410a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An electrocatalytic reaction protocol is developed for achieving intramolecular dehydrogenative annulation of N-aryl enamines. It offers a simple and efficient way for the synthesis of indoles in an undivided cell. Good to excellent yields are obtained under oxidantfree and transition-metal-free conditions. Moreover, imidazo[ 1,2-a]-pyridines could also be produced when N-pyridyl enamines were used as the substrates.

引用

页码：3354 / 3356

页数：3

共 38 条

[1] Electrochemical recycling of benzoquinone in the Pd/benzoquinone-catalyzed Heck-type reactions from arenes [J].

Amatore, Christian ;

Cammoun, Chama ;

Jutand, Anny .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (03) :292-296

[2] Cooperative electrocatalytic alcohol oxidation with electron-proton-transfer mediators [J].

Badalyan, Artavazd ;

Stahl, Shannon S. .

NATURE, 2016, 535 (7612) :406-410

[3] Copper-Catalyzed C-C Bond Formation through C-H Functionalization: Synthesis of Multisubstituted Indoles from N-Aryl Enaminones [J].

Bernini, Roberta ;

Fabrizi, Giancarlo ;

Sferrazza, Alessio ;

Cacchi, Sandro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (43) :8078-8081

[4] Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].

Cacchi, S ;

Fabrizi, G .

CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920

[5] Metal- and Reagent-Free Highly Selective Anodic Cross-Coupling Reaction of Phenols [J].

Elsler, Bernd ;

Schollmeyer, Dieter ;

Dyballa, Katrin Marie ;

Franke, Robert ;

Waldvogel, Siegfried R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (20) :5210-5213

[6] Recent advances in the electrochemical construction of heterocycles [J].

Francke, Robert .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 :2858-2873

[7] Redox catalysis in organic electrosynthesis: basic principles and recent developments [J].

Francke, Robert ;

Little, R. Daniel .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (08) :2492-2521

[8] Electrochemically Initiated Oxidative Amination of Benzoxazoles Using Tetraalkylammonium Halides As Redox Catalysts [J].

Gao, Wei-Jing ;

Li, Wei-Cui ;

Zeng, Cheng-Chu ;

Tian, Hong-Yu ;

Hu, Li-Ming ;

Little, R. Daniel .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (20) :9613-9618

[9] Preparation of indoles via iron catalyzed direct oxidative coupling [J].

Guan, Zheng-Hui ;

Yan, Ze-Yi ;

Ren, Zhi-Hui ;

Liu, Xue-Yuan ;

Liang, Yong-Min .

CHEMICAL COMMUNICATIONS, 2010, 46 (16) :2823-2825

[10] I2-Catalyzed Indole Formation via Oxidative Cyclization of N-Aryl Enamines [J].

He, Zhiheng ;

Liu, Weiping ;

Li, Zhiping .

CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (06) :1340-1343

← 1 2 3 4 →