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Iodine‐Catalyzed Formation of Amide Bond: Efficient Strategy for the Synthesis of Aromatic Primary Amides
Author(s) -
Xie Zengyang,
Chen Ruijiao,
Du Zhongyu,
Kong Lingdong,
Li Zhenquan,
Li Zhaolou,
Wang Ning,
Liu Jun
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600532
Subject(s) - chemistry , amide , iodine , catalysis , primary (astronomy) , organic chemistry , combinatorial chemistry , peptide bond , enzyme , physics , astronomy
A practical and efficient methodology for the synthesis of aromatic primary amides by reaction of benzylic alcohols and aqueous ammonia in the presence of an I 2 /TBHP system in acetonitrile was developed. This oxidative amidation proceeded smoothly at ambient temperature and tolerated a variety of functional groups. A wide range of aromatic primary amides were obtained in moderate to high yields. Preliminary kinetic studies and a possible mechanism of the oxidative amidation reaction were also discussed.