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TEMPO‐Catalyzed Aerobic Oxidative Coupling of Thiols for Metal‐Free Formation of S−N/S−S Bonds
Author(s) -
Yang Liting,
Li Shuding,
Dou Yingchao,
Zhen Shan,
Li Heng,
Zhang Panke,
Yuan Bingxin,
Yang Guanyu
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.201600588
Subject(s) - chemistry , catalysis , yield (engineering) , oxidative coupling of methane , oxidative phosphorylation , organic synthesis , coupling reaction , metal , organic chemistry , combinatorial chemistry , polymer chemistry , biochemistry , materials science , metallurgy
Catalytic syntheses of organic sulfenamides and disulfides have great significance and value in synthetic chemistry and bioscience. To establish a versatile and efficient technology for such reactions, an aerobic oxidative coupling method for the formation of S−N and S−S bonds, using TEMPO as a catalyst and O 2 as an oxidant, has been successfully developed. Reactions showed good tolerance toward various amines and thiols. Sulfenamides were produced in up to 99 % yield, while disulfides were formed in up to 97 % yield in one‐pot syntheses. Activation of the N−H bond by 2,2‐disbenzothiazoledisulfide showed the great potential in organic synthesis.
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