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Efficient Synthesis of Sulfenamides through Mitsunobu‐type Coupling Reaction of Thiols with Amines using Dibenzyl Azodicarboxylate
Author(s) -
Ryu Se Hwan,
Ra Jongmin,
Ko Haye Min
Publication year - 2020
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.202000160
Subject(s) - chemistry , mitsunobu reaction , diethyl azodicarboxylate , hydrazine (antidepressant) , dehydrogenation , organic chemistry , pericyclic reaction , coupling reaction , combinatorial chemistry , catalysis , chromatography , triphenylphosphine
S−H activation reaction of thiols employing dibenzyl azodicarboxylate (DBAD) has been developed for the preparation of sulfenamides. The dehydrogenation of thiols and amines under these reaction conditions involved the formation of dibenzyl hydrazine‐1,2‐dicarboxylate ( 5 a ), which led to the S−N bond formation reaction. The reaction proceeds efficiently with the release of 5 a and affords various sulfenamides in good to excellent yields.