B2(OH)4-Mediated Reductive Transamidation of N-Acyl Benzotriazoles with Nitro Compounds En Route to Aqueous Amide Synthesis

被引：16

作者：

Bai, Jin ^{[1
]}

Li, Shangzhang ^{[1
]}

Zhu, Riqian ^{[1
]}

Li, Yang ^{[1
]}

Li, Wanfang ^{[1
]}

机构：

[1] Univ Shanghai Sci & Technol, Sch Mat & Chem, Shanghai 200093, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 06期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; METAL-FREE TRANSAMIDATION; SECONDARY AMIDES; CARBOXYLIC-ACIDS; BOND FORMATION; ARYL HALIDES; CLEAVAGE; TETRAHYDROXYDIBORON; ACYLBENZOTRIAZOLES; HYDROGENATION;

D O I：

10.1021/acs.joc.2c02995

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We herein developed a reductive transamidation reaction between N-acyl benzotriazoles (AcBt) and organic nitro compounds or NaNO2 under mild conditions. This protocol employed the stable and readily available B-2(OH)(4) as the reducing agent and H2O as the ideal solvent. N- Deuterated amides can be synthesized when conducting the reaction in D2O. A reasonable reaction mechanism involving bond metathesis between the AcBt amide and amino boric acid intermediate was proposed to explain the unique nature of AcBt.

引用

页码：3714 / 3723

页数：10

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