Isothioureas as Coupling Partners in P-S Bond Formation through Cross-Dehydrogenative Coupling
Eimear Courtney1, Gian L Reber1, Nikita Liasiuk1
1School of Chemistry and Analytical and Biological Chemistry Research Facility (ABCRF), University College Cork, Cork T12 YN60, Ireland.
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Isothioureas have been demonstrated as practical sulfur donors for mild, one-pot P-S bond formation. Treatment with piperidine releases thiolate, which undergoes aerobic oxidation to the corresponding disulfide. Subsequent cross-dehydrogenative coupling with phosphine oxides affords phosphinothioates and related compounds in high yields. The method proceeds under air, tolerates diverse organophosphorus functional groups, and avoids malodorous reagents or external oxidants, providing an efficient and operationally simple route to P-S-containing organophosphorus compounds.
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