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三乙基硼氢化钠催化未活化酰胺可控还原为仲胺或叔胺

Sodium Triethylborohydride-Catalyzed Controlled Reduction of Unactivated Amides to Secondary or Tertiary Amines.

作者信息

Yao Wubing, He Lili, Han Deman, Zhong Aiguo

机构信息

School of Pharmaceutical and Materials Engineering , Taizhou University , Jiaojiang 318000 , Zhejiang , China.

出版信息

J Org Chem. 2019 Nov 15;84(22):14627-14635. doi: 10.1021/acs.joc.9b02211. Epub 2019 Nov 5.

DOI:10.1021/acs.joc.9b02211
PMID:31663738
Abstract

The first transition-metal-free catalytic protocol for controlled reduction of amide functions using cheap and bench-stable hydrosilanes as reducing agents has been established. By altering the hydrosilane and solvent, the new method enables the selective cleavage of unactivated C-O bonds in amides and allows the C-N bonds to selectively break via the deacylated cleavage. Overall, this novel process may offer a versatile alternative to current methodologies employing stoichiometric metal systems for the controlled reduction of carboxamides.

摘要

已经建立了首个无过渡金属催化方案,该方案使用廉价且易于保存的硅烷作为还原剂来可控地还原酰胺官能团。通过改变硅烷和溶剂,这种新方法能够选择性地裂解酰胺中未活化的C-O键,并通过脱酰基裂解使C-N键选择性断裂。总体而言,这种新方法可能为目前使用化学计量金属体系来可控还原羧酰胺的方法提供一种通用的替代方案。

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