The Phospha-Bora-Wittig Reaction

被引：35

作者：

Borys, Andryj M. ^{[1
]}

Rice, Ella F. ^{[1
]}

Nichol, Gary S. ^{[1
]}

Cowley, Michael J. ^{[1
]}

机构：

[1] Univ Edinburgh, EaStCHEM Sch Chem, Edinburgh EH9 3FJ, Midlothian, Scotland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2021年 / 143卷 / 35期

基金：

欧洲研究理事会; 英国工程与自然科学研究理事会;

关键词：

ORGANIC-CHEMISTRY; DOUBLE-BOND; COMPLEXES; SINGLE; P=C; PHOSPHINOBORATION; ACTIVATION; MOLECULES; MECHANISM; ALDEHYDES;

D O I：

10.1021/jacs.1c06228

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report the phospha-bora-Wittig reaction for the direct preparation of phosphaalkenes from aldehydes, ketones, esters, or amides. The transient phosphaborene Mes*P=B-NR2 reacts with carbonyl compounds to form 1,2,3-phosphaboraoxetanes, analogues of oxaphosphetane intermediates in the classical Wittig reaction. 1,2,3-Phosphaboraoxetanes undergo thermal or Lewis acid-promoted cycloreversion, yielding phosphaalkenes. Experimental and density functional theory studies reveal far-reaching similarities between classical and phospha-bora-Wittig reactions.

引用

页码：14065 / 14070

页数：6

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