Access to Nitriles from Aldehydes Mediated by an Oxoammonium Salt

被引：99

作者：

Kelly, Christopher B. ^{[1
]}

Lambert, Kyle M. ^{[1
]}

Mercadante, Michael A. ^{[1
]}

Ovian, John M. ^{[1
]}

Bailey, William F. ^{[1
]}

Leadbeater, Nicholas E. ^{[1
,2
]}

机构：

[1] Univ Connecticut, Dept Chem, Storrs, CT 06269 USA

[2] Univ Connecticut, Ctr Hlth, Dept Community Med & Hlth Care, Exchange, Farmington, CT 06030 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 14期

基金：

美国国家科学基金会;

关键词：

aldehydes; cyanides; oxidation; reaction mechanisms; synthetic methods; PRIMARY AMINES; OXIDATIVE SYNTHESIS; AEROBIC OXIDATION; PRIMARY ALCOHOLS; AQUEOUS AMMONIA; PRIMARY AMIDES; EFFICIENT; CONVERSION; DEHYDRATION; ALDOXIMES;

D O I：

10.1002/anie.201412256

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A scalable, high yielding, rapid route to access an array of nitriles from aldehydes mediated by an oxoammonium salt (4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) and hexamethyldisilazane (HMDS) as an ammonia surrogate has been developed. The reaction likely involves two distinct chemical transformations: reversible silyl-imine formation between HMDS and an aldehyde, followed by oxidation mediated by the oxoammonium salt and desilylation to furnish a nitrile. The spent oxidant can be easily recovered and used to regenerate the oxoammonium salt oxidant.

引用

页码：4241 / 4245

页数：5

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