Premium
Amide Synthesis from Thiocarboxylic Acids and Amines by Spontaneous Reaction and Electrosynthesis
Author(s) -
Tang Li,
Matuska Jack H.,
Huang YuHan,
He YanHong,
Guan Zhi
Publication year - 2019
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201900814
Subject(s) - amide , electrosynthesis , chemistry , catalysis , organic chemistry , green chemistry , combinatorial chemistry , primary (astronomy) , reaction mechanism , electrochemistry , physics , electrode , astronomy
Amide bond formation is one of the most important basic reactions in chemistry. A catalyst‐free approach for constructing amide bonds from thiocarboxylic acids and amines was developed. The mechanistic studies showed that the disulfide was the key intermediate for this amide synthesis. Thiobenzoic acids could be automatically oxidized to disulfides in air, thioaliphatic acids could be electro‐oxidized to disulfides, and the resulting disulfides reacted with amines to give the corresponding amides. By this method, various amides could be easily synthesized in excellent yields without using any catalyst or activator. The successful synthesis of bioactive compounds also highlights the synthetic utility of this strategy in medicinal chemistry.