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
收藏
页码：1958 / 1961
页数：4
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