Ammonia-borane as a Catalyst for the Direct Amidation of Carboxylic Acids

被引：36

作者：

Ramachandran, P. Veeraraghavan ^{[1
]}

Hamann, Henry J. ^{[1
]}

机构：

[1] Purdue Univ, Herbert C Brown Ctr Borane Res, Dept Chem, W Lafayette, IN 47907 USA

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 08期

关键词：

CHEMISTRY RESEARCH AREAS; ALPHA-AMINO-ACIDS; ORAL DELIVERY; BORIC-ACID; PERSPECTIVE; ACTIVATION; MECHANISMS; AMIDES;

D O I：

10.1021/acs.orglett.1c00591

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ammonia-borane serves as an efficient substoichiometric (10%) precatalyst for the direct amidation of both aromatic and aliphatic carboxylic acids. In situ generation of amine-boranes precedes the amidation and, unlike the amidation with stoichiometric amine-boranes, this process is facile with 1 equiv of the acid. This methodology has high functional group tolerance and chromatography-free purification but is not amenable for esterification. The latter feature has been exploited to prepare hydroxyl- and thiol-containing amides.

引用

页码：2938 / 2942

页数：5

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