A general and practical method of alkynyl indole and benzofuran synthesis via tandem Cu- and Pd-catalyzed cross-couplings

被引：164

作者：

Nagamochi, Masatoshi ^{[1
]}

Fang, Yuan-Qing ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Davenport Res Labs, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 15期

关键词：

D O I：

10.1021/ol071370w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new tandem coupling approach to synthesize 2-alkynyl indoles and benzofurans is described. This reaction utilizes easily accessible gem-dibromovinyl substrates and terminal alkynes and proceeds via Pd/C- and CuI-catalyzed tandem Ullman/Sonogashira couplings.

引用

页码：2955 / 2958

页数：4

共 28 条

[11]

Donelly D. M. X., 1984, COMPREHENSIVE HETERO, V4, P657

[12] Pd-catalyzed tandem C-N/C-C coupling of gem-dihalovinyl systems: A modular synthesis of 2-substituted indoles [J].

Fang, YQ ;

Lautens, M .

ORGANIC LETTERS, 2005, 7 (16) :3549-3552

[13]

FANG YQ, 2007, J ORG CHEM 0609

[14] Efficient syntheses of KDR kinase inhibitors using a Pd-catalyzed tandem C-N/Suzuki coupling as the key step [J].

Fang, Yuan-Qing ;

Karisch, Robert ;

Lautens, Mark .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1341-1346

[15] High-turnover palladium catalysts in cross-coupling and Heck chemistry: A critical overview [J].

Farina, V .

ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1553-1582

[16] Synthesis of 2-vinylic indoles and derivatives via a Pd-catalyzed tandem coupling reaction [J].

Fayol, Aude ;

Fang, Yuan-Qing ;

Lautens, Mark .

ORGANIC LETTERS, 2006, 8 (19) :4203-4206

[17] Pd/C: An old catalyst for new applications - Its use for the Suzuki-Miyaura reaction [J].

Felpin, Francois-Xavier ;

Ayad, Tahar ;

Mitra, Soumya .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (12) :2679-2690

[18] Recent developments in indole ring synthesis-methodology and applications [J].

Gribble, GW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (07) :1045-1075

[19] Practical methodologies for the synthesis of indoles [J].

Humphrey, Guy R. ;

Kuethe, Jeffrey T. .

CHEMICAL REVIEWS, 2006, 106 (07) :2875-2911

[20] Palladium-catalyzed synthesis of butatrienes [J].

Ogasawara, M ;

Ikeda, H ;

Ohtsuki, K ;

Hayashi, T .

CHEMISTRY LETTERS, 2000, (07) :776-777

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