An (NH4)2S2O8-promoted cross-coupling of thiols/diselenides and sulfoxides for the synthesis of unsymmetrical disulfides/selenosulfides. 2022

Yang-Tong Ma, and Chao Lin, and Xiao-Bo Huang, and Miao-Chang Liu, and Yun-Bing Zhou, and Hua-Yue Wu
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, 325035, P. R. China. mcl@wzu.edu.cn.

An (NH4)2S2O8-promoted cross-coupling of thiols/diselenides and sulfoxides to construct unsymmetrical disulfides/selenosulfides is disclosed. Control experiments demonstrate that (NH4)2S2O8 acts as an acid and an oxidant, while both ionic and radical routes are involved in the reaction. The KIE experiments reveal that C-H bond cleavage of sulfoxides was involved in the turnover-limiting step.

UI MeSH Term Description Entries
D004220 Disulfides Chemical groups containing the covalent disulfide bonds -S-S-. The sulfur atoms can be bound to inorganic or organic moieties. Disulfide
D013438 Sulfhydryl Compounds Compounds containing the -SH radical. Mercaptan,Mercapto Compounds,Sulfhydryl Compound,Thiol,Thiols,Mercaptans,Compound, Sulfhydryl,Compounds, Mercapto,Compounds, Sulfhydryl
D013454 Sulfoxides Organic compounds that have the general formula R-SO-R. They are obtained by oxidation of mercaptans (analogous to the ketones). (From Hackh's Chemical Dictionary, 4th ed)

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