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
收藏
页码：8995 / 9001
页数：7
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