Conjugated oxidation of thiols and amines in the presence of copper complexes

The oxidation of aliphatic thiols by air oxygen under mild conditions catalyzed by copper(II) complexes with amines (e.g. benzylamine) has been investigated. It was found that the reaction proceeds as a conjugated oxidation of both amines and thiols. The products of transformation of benzylamine hav...

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Bibliographic Details
Published in:Reaction kinetics, mechanisms and catalysis mechanisms and catalysis, 2010-12, Vol.101 (2), p.267-278
Main Authors: Tarkhanova, I. G., Gantman, M. G., Chizhov, A. O., Smirnov, V. V.
Format: Article
Language:English
Subjects:
Catalysis
Chemistry
Chemistry and Materials Science
Industrial Chemistry/Chemical Engineering
Physical Chemistry
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Summary:The oxidation of aliphatic thiols by air oxygen under mild conditions catalyzed by copper(II) complexes with amines (e.g. benzylamine) has been investigated. It was found that the reaction proceeds as a conjugated oxidation of both amines and thiols. The products of transformation of benzylamine have been identified. Copper(I) dodecanethiolate was synthesized for the first time, and its composition was determined. The thiolate is shown to be an intermediate of the process in the systems which demonstrate low activity. The intermediate in the most active systems is a mixed-ligand copper(II) complex containing both molecules of amine and thiolate anions in the coordination sphere.
ISSN:1878-5190
1878-5204
DOI:10.1007/s11144-010-0230-y