Synthesis of 2-vinylic indoles and derivatives via a Pd-catalyzed tandem coupling reaction

被引：158

作者：

Fayol, Aude ^{[1
]}

Fang, Yuan-Qing ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 19期

关键词：

D O I：

10.1021/ol061374l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel one-step synthesis of valuable 2-vinylic indoles and their tricycle derivatives is described. This reaction, which utilizes a gemdibromovinyl unit as a readily available starting material, occurs via an efficient Pd-catalyzed tandem Buchwald-Hartwig/Heck reaction.

引用

页码：4203 / 4206

页数：4

共 58 条

[21] SYNTHESIS OF 2-ARYL-1H-INDOLES AND 2-VINYL-1H-INDOLES VIA PALLADIUM-CATALYZED CROSS-COUPLING OF ARYL AND VINYL HALIDES WITH 1-CARBOXY-2-(TRIBUTYLSTANNYL)INDOLE [J].

HUDKINS, RL ;

DIEBOLD, JL ;

MARSH, FD .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) :6218-6220

[22] On the efficiency of tetraalkylammonium salts in Heck type reactions [J].

Jeffery, T .

TETRAHEDRON, 1996, 52 (30) :10113-10130

[23]

Jiang L., METAL CATALYZED CROS

[24] Synthesis of conjugated enediynes via palladium catalyzed cross-coupling reactions of potassium alkynyltrifluoroborates [J].

Kabalka, GW ;

Dong, G ;

Venkataiah, B .

TETRAHEDRON LETTERS, 2005, 46 (05) :763-765

[25] C-H activation and palladium migration within biaryls under Heck reaction conditions [J].

Karig, G ;

Moon, MT ;

Thasana, N ;

Gallagher, T .

ORGANIC LETTERS, 2002, 4 (18) :3115-3118

[26] Synthesis of isocoumarins and α-pyrones via palladium-catalyzed annulation of internal alkynes [J].

Larock, RC ;

Doty, MJ ;

Han, XJ .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (24) :8770-8779

[27] 3-cyanomethyl-2-vinylindoles as thermal indole-2,3-quinodimethane equivalents: synthesis of functionalized 1,2,3,4-tetrahydrocarbazoles [J].

Laronze, M ;

Sapi, J .

TETRAHEDRON LETTERS, 2002, 43 (44) :7925-7928

[28] 1,4-Migration of rhodium and palladium in catalytic organometallic reactions [J].

Ma, SM ;

Gu, ZH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (46) :7512-7517

[29] Bicyclic carbopalladation reaction with two gem-reaction centers.: Efficient construction of fused bicyclic skeletons [J].

Ma, SM ;

Xu, B .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9156-9157

[30] Studies on the oxidative addition reaction of 1,1-dibromo-1-alkenes, α-dehalopalladation, and the intramolecular bis(carbopalladation) reaction of alkenes.: An efficient entry to fused bicycles [J].

Ma, SM ;

Xu, B ;

Ni, BK .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (25) :8532-8543

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