Selective Ruthenium-Catalyzed Hydrochlorination of Alkynes: One-Step Synthesis of Vinylchlorides

被引：50

作者：

Derien, Sylvie ^{[1
]}

Klein, Hubert ^{[1
]}

Bruneau, Christian ^{[1
]}

机构：

[1] Univ Rennes 1, CNRS, Inst Sci Chim Rennes, UMR 6226, F-35042 Rennes, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 41期

关键词：

alkenes; alkynes; hydrohalogenation; ruthenium; synthetic methods; HIGHLY STEREOSELECTIVE-SYNTHESIS; C BOND FORMATION; VINYL CHLORIDES; HYDROGEN-CHLORIDE; TERMINAL ALKYNES; AROYL CHLORIDES; ACID-CHLORIDES; BORONIC ACIDS; HALIDES; HYDROHALOGENATION;

D O I：

10.1002/anie.201505144

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unprecedented ruthenium-catalyzed direct and selective alkyne hydrochlorination is reported and leads to vinylchlorides in excellent yields with atom economy. The reaction proceeds at room temperature from terminal alkynes and provides a variety of chloroalkenes. Only the regioisomer resulting from the formal Markovnikov addition is selectively formed. Mechanistic studies show the stereoselective syn addition of HCl to alkynes at room temperature and suggest a chloro hydrido Ru-IV species as a key intermediate of the reaction.

引用

页码：12112 / 12115

页数：4

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