METAL EXCHANGE BETWEEN AN ELECTROGENERATED ORGANONICKEL SPECIES AND ZINC HALIDE - APPLICATION TO AN ELECTROCHEMICAL, NICKEL-CATALYZED REFORMATSKY REACTION

被引：59

作者：

CONAN, A ^{[1
]}

SIBILLE, S ^{[1
]}

PERICHON, J ^{[1
]}

机构：

[1] CNRS,UMR 28,ELECTROCHIM CATALYSE & SYNTH ORGAN LAB,2 RUE HENRI DUNANT,F-94320 THIAIS,FRANCE

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 06期

关键词：

D O I：

10.1021/jo00006a012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mechanism of the electroreductive coupling of alpha-chloro esters or alpha-chloro nitriles with carbonyl compounds by the means of a sacrificial zinc anode and a nickel catalyst was elucidated by electroanalytical techniques. The mechanism involved reduction of a Ni(II) complex to a Ni(0) complex, oxidative addition of the alpha-chloro ester to the Ni(0) complex, and a Zn(II)/Ni(II) exchange, leading to an organozinc Reformatsky reagent. The electrosynthesis of various beta-hydroxy esters, beta-hydroxy nitriles, and 2,3-epoxy esters was successfully achieved under extremely mild conditions.

引用

页码：2018 / 2024

页数：7

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