An efficient route to 2,3-disubstituted indoles via reductive alkylation using H2 as reductant

被引：27

作者：

Cao, Liang-Liang ^{[1
]}

Wang, Duo-Sheng ^{[2
]}

Jiang, Guo-Fang ^{[1
]}

Zhou, Yong-Gui ^{[2
]}

机构：

[1] Hunan Univ, Coll Chem & Chem Engn, Changsha 410082, Hunan, Peoples R China

[2] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 22期

基金：

中国国家自然科学基金;

关键词：

2,3-Disubstituted indoles; Reductive alkylation; Pd/C H-2; PALLADIUM-CATALYZED REACTION; SOLID-PHASE SYNTHESIS; 2-ALKYNYLTRIFLUOROACETANILIDES; FUNCTIONALIZATION;

D O I：

10.1016/j.tetlet.2011.03.099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient route to 2,3-disubstituted indoles was developed via reductive alkylation of 2-substituted indoles using hydrogen as a clean and atom economic reductant under ambient pressure. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：2837 / 2839

页数：3

共 29 条

[1] Novel routes to pyrroles, indoles and carbazoles -: Applications in natural product synthesis [J].

Agarwal, S ;

Cämmerer, S ;

Filali, S ;

Fröhner, W ;

Knöll, J ;

Krahl, MP ;

Reddy, KR ;

Knölker, HJ .

CURRENT ORGANIC CHEMISTRY, 2005, 9 (15) :1601-1614

[2] A MILD AND SELECTIVE C-3 REDUCTIVE ALKYLATION OF INDOLES [J].

APPLETON, JE ;

DACK, KN ;

GREEN, AD ;

STEELE, J .

TETRAHEDRON LETTERS, 1993, 34 (09) :1529-1532

[3] 3-(2-Alken-1-one-2-yl)indoles through the palladium-catalyzed reaction of 2-alkynyltrifluoroacetanilides with cyclic α-iodoenones [J].

Arcadi, Antonio ;

Cianci, Roberto ;

Ferrara, Giovanni ;

Marinelli, Fabio .

TETRAHEDRON, 2010, 66 (13) :2378-2383

[4]

Bandini M., 2009, Catalytic Asymmetric Friedel-Crafts Alkylations

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

Bandini, Marco ;

Eichholzer, Astrid .

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

[6] Recent Advances in the Synthesis of Indole and Quinoline Derivatives through Cascade Reactions [J].

Barluenga, Jose ;

Rodriguez, Felix ;

Fananas, Francisco J. .

CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (07) :1036-1048

[7] Organocatalytic strategies for the asymmetric functionalization of indoles [J].

Bartoli, Giuseppe ;

Bencivenni, Giorgio ;

Dalpozzo, Renato .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (11) :4449-4465

[8] Domino rhodium(I)-catalysed reactions for the efficient synthesis of substituted benzofurans and indoles [J].

Boyer, Alistair ;

Isono, Naohiro ;

Lackner, Sebastian ;

Lautens, Mark .

TETRAHEDRON, 2010, 66 (33) :6468-6482

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

Cacchi, S ;

Fabrizi, G .

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

[10] 2,3-Disubstituted Indoles via Palladium-Catalyzed Reaction of 2-Alkynyltrifluoroacetanilides with Arenediazonium Tetrafluoroborates [J].

Cacchi, Sandro ;

Fabrizi, Giancarlo ;

Goggiamani, Antonella ;

Perboni, Alcide ;

Sferrazza, Alessio ;

Stabile, Paolo .

ORGANIC LETTERS, 2010, 12 (14) :3279-3281

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