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.
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