Sustainable Approach to Azaheterocyclic Acetamides by Decarboxylative Aminoformylation

• Published in: ACS sustainable chemistry & engineering 2020-11, Vol.8 (44), p.16463-16468
• Main Authors: Zhang, Zhenxing, Jia, Chunqi, Kong, Xiangtao, Hussain, Muzammal, Liu, Zhenyu, Liang, Wanqing, Jiang, Ling, Jiang, Hao, Ma, Junyan
• Format: Article
• Language: English
• ISSN: 2168-0485; 2168-0485
• DOI: 10.1021/acssuschemeng.0c05118

A green and efficient synthesis of azaheterocyclic acetamides has been developed that significantly reduces the consumption of nitrogen-containing reagents from more than 20 equiv in previously reported methods to 1.5 equiv. This reduction decreased both the pollution potential and cost, especially if the nitrogen-containing reagent is expensive and difficult to recycle. Therefore, this strategy is environmentally friendly and sustainable. Moreover, this process uses economical inorganic peroxysulfate as an oxidant to initiate the difunctionalization of alkenes via aminoformyl radicals and aryl C­(sp2)–H bonds, providing efficient and sustainable access to a broad substrate scope and promising functional group tolerance. Notably, a series of unreported dioxoisoquinolines and oxindole derivatives were synthesized by applying this green method, which highlights its potential utility in medicine-related clinical research.