One-pot synthesis of N-methylindoles from N-methylanilines and of benzofurans from phenols using transition-metal carbene X-H insertion reactions

被引：32

作者：

Honey, Mark A. ^{[1
]}

Blake, Alexander J. ^{[1
]}

Campbell, Ian B. ^{[2
]}

Judkins, Brian D. ^{[2
]}

Moody, Christopher J. ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] GlaxoSmithKline, Stevenage SG1 2NY, Herts, England

来源：

TETRAHEDRON | 2009年 / 65卷 / 44期

基金：

英国工程与自然科学研究理事会;

关键词：

HIGHLY ENANTIOSELECTIVE INSERTION; RHODIUM CARBENOIDS; ETHYL DIAZOACETATE; DIAZO-COMPOUNDS; DIAZOCARBONYL; BONDS; DERIVATIVES; INDOLES; ACID;

D O I：

10.1016/j.tet.2009.07.077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Transition-metal carbene X-H insertion reactions (X=N or O) have been employed in the simple conversion of anilines and phenols into indoles and benzofurans, respectively. Thus copper(II) catalyzed N-H insertion reactions of alpha-diazo-beta-ketoesters with N-methylanilines followed by treatment with acidic ion-exchange resin gives indoles. In a similar manner, dirhodium(II) catalyzed O-H insertion reactions of alpha-diazo-beta-ketoesters with phenols followed by treatment with PPA gives benzofurans. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：8995 / 9001

页数：7

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