Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles

被引：113

作者：

Chen, Yifeng ^{[1
]}

Romaire, Justin P. ^{[1
]}

Newhouse, Timothy R. ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 18期

关键词：

ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; SILYL ENOL ETHERS; REDUCTIVE ELIMINATION; AEROBIC DEHYDROGENATION; SYNTHETIC REACTIONS; PRACTICAL SYNTHESIS; ORGANIC-SYNTHESIS; KETONES; COMPLEXES; REAGENTS;

D O I：

10.1021/jacs.5b02243

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly practical and general palladium-catalyzed methodology for the alpha,beta-dehydrogenation of esters and nitriles is repotted. Generation of a zinc enolate or (cyanoalkyl)zinc species followed by the addition of an allyl oxidant and a palladium catalyst results in synthetically useful yields of alpha,beta-unsaturated esters, lactones, and nitriles. Preliminary mechanistic investigations are consistent with reversible beta-hydride elimination and turnover-limiting, propene-forming reductive elimination.

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页码：5875 / 5878

页数：4

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