Categories: C-S Bond Formation >
Synthesis of dithiocarbonates (xanthates)
S-Arylation of potassium O-alkyl xanthates with diaryliodonium salts proceeds under mild conditions, enabling access to substituted S-aryl xanthates. The method exhibits good functional group tolerance and can be applied to the late-stage C-H functionalization of drug molecules. Divergent transformations of the resulting S-aryl xanthates provide a range of organosulfur compounds.
D. I. Bugaenko, A. A. Volkov, V. V. Andreychev, A. V. Karchava, Org. Lett., 2023, 25, 272-276.
A simple and efficient method to obtain α-xanthylmethyl ketones from α-diazo ketones proceeds through a protonation/nucleophilic substitution sequence in the presence of p-toluenesulfonic acid and potassium ethyl xanthogenate as the nucleophile. The reaction provides a broad variety of xanthates.
P. López-Mendoza, L. D. Miranda, Synthesis, 2021, 53, 3777-3790.
In an efficient Cu-catalyzed one-pot approach for the synthesis of unsymmetrical diaryl thioethers through a Cu-catalyzed double arylation, the aryl thiols are generated in situ from an easily available xanthate and aryl halides. This strategy was further successfully utilized for the synthesis of symmetrical diaryl thioethers, aryl alkyl thioethers, and benzothiazoles.
D. J. C. Prasad, G. Sekar, Org. Lett., 2011, 13, 1008-1011.