Synthesis of Functionalized Benzo[b]thiophenes by the Intramolecular Copper-Catalyzed Carbomagnesiation of Alkynyl(aryl)thioethers

被引：70

作者：

Kunz, Thomas ^{[1
]}

Knochel, Paul ^{[1
]}

机构：

[1] Univ Munich, Dept Chem, D-81377 Munich, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 08期

基金：

欧洲研究理事会;

关键词：

benzo[b]thiophenes; carbomagnesiation; copper catalysis; cyclization; heterocycle synthesis; HIGHLY SELECTIVE SYNTHESIS; CROSS-COUPLING REACTION; ELECTROPHILIC CYCLIZATION; ELIMINATION REACTION; EFFICIENT SYNTHESIS; DERIVATIVES; HALIDES; ALKYNES; REAGENTS; INDOLE;

D O I：

10.1002/anie.201106734

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Highly functional: A copper(I)-catalyzed intramolecular carbomagnesiation under mild conditions transforms readily available alkynyl(aryl)thioethers into magnesiated benzothiophenes. Subsequent reaction with various electrophiles (acid chlorides, allyl bromides, aryl halides) provides polyfunctional benzo[b]thiophenes (see scheme). Further modification of the cyclization products affords highly diversified benzothiophene derivatives and new heterocyclic scaffolds. © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1958 / 1961

页数：4

共 70 条

[1] Zinc Homologation-Elimination Reaction of α-Sulfinyl Carbanions as a New Route to Olefins [J].