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

被引：163

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

[1]

Anderson N. G., 2000, PRACTICAL PROCESS RE

[2]

Bird C W., 1984, COMPREHENSIVE HETERO, P89

[3]

BLEICHER L, 1995, SYNLETT, P1115

[4]

BREICHER LS, 1998, J ORG CHEM, V63, P1109

[5] Industrial-scale palladium-catalyzed coupling of aryl halides and amines - A personal account [J].

Buchwald, SL ;

Mauger, C ;

Mignani, G ;

Scholz, U .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) :23-39

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

Cacchi, S ;

Fabrizi, G .

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

[7]

Cagniant P., 1975, Adv. Heterocycl. Chem., V18, P337, DOI DOI 10.1016/S0065-2725(08)60132-4

[8] Synthesis of benzo[b]furans via CuI-catalyzed ring closure [J].

Chen, CY ;

Dormer, PG .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17) :6964-6967

[9] (S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine Maleate (SIB-1508Y): A novel anti-Parkinsonian agent with selectivity for neuronal nicotinic acetylcholine receptors [J].

Cosford, NDP ;

Bleicher, L ;

Herbaut, A ;

McCallum, JS ;

Vernier, JM ;

Dawson, H ;

Whitten, JP ;

Adams, P ;

ChavezNoriega, L ;

Correa, LD ;

Crona, JH ;

Mahaffy, LS ;

Menzaghi, F ;

Rao, TS ;

Reid, R ;

Sacaan, AI ;

Santori, E ;

Stauderman, KA ;

Whelan, K ;

Lloyd, GK ;

McDonald, IA .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (17) :3235-3237

[10] CROSS-COUPLING REACTIONS OF MONOSUBSTITUTED ACETYLENES AND ARYL HALIDES CATALYZED BY PALLADIUM ON CHARCOAL [J].

DELAROSA, MA ;

VELARDE, E ;

GUZMAN, A .

SYNTHETIC COMMUNICATIONS, 1990, 20 (13) :2059-2064

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