Copper- or phosphine-catalyzed reaction of alkynes with isocyanides. Regioselective synthesis of substituted pyrroles controlled by the catalyst

被引：295

作者：

Kamijo, S ^{[1
]}

Kanazawa, C ^{[1
]}

Yamamoto, Y ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 25期

关键词：

D O I：

10.1021/ja051875m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The copper-catalyzed reaction of isocyanides (CNCH(2)EWG(1)) 1 with electron-deficient alkynes (RC equivalent to CEWG(2)) 2 gave the 2,4-di-EWG-substituted pyrroles 3 selectively, whereas the phosphine-catalyzed reaction of 1 with 2 afforded the 2,3-di-EWG-subsituted pyrroles 4. Accordingly, regioselective synthesis of substituted pyrroles has been achieved by merely choosing the catalyst.

引用

页码：9260 / 9266

页数：7

共 79 条

[1] Synthesis of γ,δ-didehydrohomoglutamates by the phosphine-catalyzed γ-addition reaction to acetylenic esters [J].

Alvarez-Ibarra, C ;

Csáky, AG ;

de la Oliva, CG .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) :3544-3547

[2]

[Anonymous], 1992, CONJUGATED ADDITION

[3]

[Anonymous], 1984, COMPREHENSIVE HETERO

[4] Pyrrole syntheses by multicomponent coupling reactions [J].

Balme, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (46) :6238-6241

[5] A NEW SYNTHESIS OF PYRROLES FROM NITROALKENES [J].

BARTON, DHR ;

ZARD, SZ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (16) :1098-1100

[6]

Black D. S., 2001, SCI SYNTHESIS, P441

[7] ENHANCEMENT OF THE EQUILIBRIUM ACIDITIES OF CARBON ACIDS BY POLYFLUOROARYL SUBSTITUENTS [J].

BORDWELL, FG ;

BRANCA, JC ;

BARES, JE ;

FILLER, R .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (04) :780-782

[8] A room temperature stable 1,3-diphosphaallyl radical [J].

Canac, Y ;

Baceiredo, A ;

Schoeller, WW ;

Gigmes, D ;

Bertrand, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (32) :7579-7580

[9]

Carruthers W, 1990, Cycloaddition Reactions in Organic Synthesis

[10] Effect of fluorine substitution on the carbon acidity of methane, methyl isocyanide, acetonitrile, acetaldehyde, and nitromethane [J].

Castejon, HJ ;

Wiberg, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12) :3937-3942

← 1 2 3 4 5 6 7 8 →