Rhodium-Catalyzed Regioselective Ortho C-H Olefination of 2-Arylindoles via NH-Indole-Directed C-H Bond Cleavage

被引：31

作者：

Han, Qingshuai ^{[1
]}

Guo, Xiemin ^{[1
]}

Tang, Ziyuan ^{[1
]}

Su, Lv ^{[1
]}

Yao, Zizhu ^{[1
]}

Zhang, Xiaofeng ^{[1
]}

Lin, Shen ^{[1
]}

Xiang, Shengchang ^{[2
]}

Huang, Qiufeng ^{[1
,2
]}

机构：

[1] Fujian Normal Univ, Coll Chem & Mat Sci, Fuzhou 350007, Fujian, Peoples R China

[2] Fujian Key Lab Polymer Mat, Fuzhou 350007, Fujian, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 05期

基金：

中国国家自然科学基金;

关键词：

rhodium-catalyzed; C-H activation; olefination; 2-arylindoles; MELATONIN RECEPTOR; C-3; ALKENYLATION; DIRECT ARYLATION; FUNCTIONALIZATION; PYRROLES; ACTIVATION; C2-ALKENYLATION; CONSTRUCTION; ALKYNES; UPDATE;

D O I：

10.1002/adsc.201701381

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

In the past decades, C-H oxidative olefination of indole at C-2, C-3, C-4 and C-7 positions was well addressed. We report here a rhodium-catalyzed NH-indole-directed ortho C-H bond olefination of 2-arylindoles. This cross-dehydrogenative-coupling proved to be broad in substrate scope, tolerating a variety of functional groups. The synthesis of 6H-isoindolo[2,1-]indoles via rhodium-catalyzed ortho C-H olefination and subsequent intramolecular aza-Michael reaction of 2-arylindoles was also demonstrated.

引用

页码：972 / 984

页数：13

共 57 条

[1] Ruthenium-catalyzed aerobic oxidative coupling of alkynes with 2-aryl-substituted pyrroles [J].

Ackermann, Lutz ;

Wang, Lianhui ;

Lygin, Alexander V. .

CHEMICAL SCIENCE, 2012, 3 (01) :177-180

[2]

[Anonymous], 2008, ANGEW CHEM INT EDIT

[3]

[Anonymous], 2016, ANGEW CHE

[4] Palladium-Catalyzed Olefination of Aryl C-H Bonds by Using Directing Scaffolds [J].

Bag, Sukdev ;

Maiti, Debabrata .

SYNTHESIS-STUTTGART, 2016, 48 (06) :804-815

[5]

Bandini M., 2009, ANGEW CHEM, V121, P9786, DOI DOI 10.1002/ange.200901843

[6] Catalytic Functionalization of Indoles in a New Dimension [J].

Bandini, Marco ;

Eichholzer, Astrid .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644

[7] Divergent synthesis of isoindolo[2,1-a]indole and indolo[1,2-a]indole through copper-catalysed C- and N-arylations [J].

Barbero, Nekane ;

SanMartin, Raul ;

Dominguez, Esther .

TETRAHEDRON LETTERS, 2009, 50 (18) :2129-2131

[8] Update 1 of: Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions [J].

Cacchi, Sandro ;

Fabrizi, Giancarlo .

CHEMICAL REVIEWS, 2011, 111 :PR215-PR283

[9] Directed palladation: fine tuning permits the catalytic 2-alkenylation of indoles [J].

Capito, E ;

Brown, JM ;

Ricci, A .

CHEMICAL COMMUNICATIONS, 2005, (14) :1854-1856

[10] Palladium-Catalyzed Intermolecular C3 Alkenylation of Indoles Using Oxygen as the Oxidant [J].

Chen, Wen-Liang ;

Gao, Ya-Ru ;

Mao, Shuai ;

Zhang, Yan-Lei ;

Wang, Yu-Fei ;

Wang, Yong-Qiang .

ORGANIC LETTERS, 2012, 14 (23) :5920-5923

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