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Isothioureas as coupling partners in P–S bond formation through cross-dehydrogenative coupling
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Date
2025-12-19
Authors
Courtney, Eimear
Reber, Gian L.
Liasiuk, Nikita
Jones, David J.
Journal Title
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Volume Title
Publisher
American Chemical Society (ACS)
Published Version
Abstract
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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Keywords
Chemical synthesis , Disulfides , Organophosphorus compounds , Piperidines , Sulfur
Citation
Courtney, E., Reber, G. L., Liasiuk, N. and Jones, D. J. (2025) 'Isothioureas as coupling partners in P–S bond formation through cross-dehydrogenative coupling', Organic Letters. https://doi.org/10.1021/acs.orglett.5c04813
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© 2025, American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters after technical editing by the publisher. To access the final edited and published work see: https://doi.org/10.1021/acs.orglett.5c04813