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电化学酰胺化:苯甲酰肼/卡巴肼和胺作为偶联伙伴。

Electrochemical Amidation: Benzoyl Hydrazine/Carbazate and Amine as Coupling Partners.

机构信息

Department of Chemistry, Indian Institute of Technology Guwahati, North Guwahati 781039, India.

出版信息

Org Lett. 2022 Sep 16;24(36):6619-6624. doi: 10.1021/acs.orglett.2c02626. Epub 2022 Sep 7.

Abstract

An electrochemical amidation of benzoyl hydrazine/carbazate and primary/secondary amine as coupling partners via concomitant cleavage and formation of C(sp)-N bonds has been achieved. This methodology proceeds under metal-free and exogenous oxidant-free conditions producing N and H as byproducts. Mechanistic studies reveal the generations of both acyl and -centered radicals from benzoyl hydrazines and amines. The utility of this protocol is demonstrated through a large-scale, and synthesis of bezafibrate, a hyperlipidemic drug.

摘要

通过同时断裂和形成 C(sp)-N 键,实现了苯甲酰腙/脒与伯/仲胺作为偶联伙伴的电化学酰胺化。该方法在无金属和无外源氧化剂的条件下进行,生成 N 和 H 作为副产物。机理研究表明,苯甲酰腙和胺均生成了酰基和 -中心自由基。该方法通过大规合成降脂药苯扎贝特得到了验证。

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