Frustrated Lewis Pair Mediated 1,2-Hydrocarbation of Alkynes

被引：21

作者：

Fasano, Valerio ^{[1
]}

Curless, Liam D. ^{[1
]}

Radcliffe, James E. ^{[1
]}

Ingleson, Michael J. ^{[1
]}

机构：

[1] Univ Manchester, Sch Chem, Oxford Rd, Manchester M13 9PL, Lancs, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 31期

基金：

英国工程与自然科学研究理事会;

关键词：

alkynes; carbocations; frustrated Lewis pairs; hydride transfer; 1,2-hydrocarbation; SIGMA-BOND ACTIVATION; ALKENES; ACIDS; B(C6F5)(3); REACTIVITY; ADDITIONS; SALTS;

D O I：

10.1002/anie.201705100

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Frustrated Lewis pair (FLP) chemistry enables a rare example of alkyne 1,2-hydrocarbation with N-methyl-acridinium salts as the carbon Lewis acid. This 1,2-hydrocarbation process does not proceed through a concerted mechanism as in alkyne syn-hydroboration, or through an intramolecular 1,3-hydride migration as operates in the only other reported alkyne 1,2-hydrocarbation reaction. Instead, in this study, alkyne 1,2-hydrocarbation proceeds by a novel mechanism involving alkyne dehydrocarbation with a carbon Lewis acid based FLP to form the new C-C bond. Subsequently, intermolecular hydride transfer occurs, with the Lewis acid component of the FLP acting as a hydride shuttle that enables alkyne 1,2-hydrocarbation.

引用

页码：9202 / 9206

页数：5

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