Isothioureas as coupling partners in P–S bond formation through cross-dehydrogenative coupling

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dc.check.date2026-12-19en
dc.check.infoAccess to this article is restricted until 12 months after publication by request of the publisheren
dc.contributor.authorCourtney, Eimearen
dc.contributor.authorReber, Gian L.en
dc.contributor.authorLiasiuk, Nikitaen
dc.contributor.authorJones, David J.en
dc.contributor.funderResearch Irelanden
dc.date.accessioned2025-12-22T10:26:32Z
dc.date.available2025-12-22T10:26:32Z
dc.date.issued2025-12-19en
dc.description.abstractIsothioureas 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.en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationCourtney, 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.5c04813en
dc.identifier.doi10.1021/acs.orglett.5c04813en
dc.identifier.issn1523-7060en
dc.identifier.issn1523-7052en
dc.identifier.journaltitleOrganic Lettersen
dc.identifier.urihttps://hdl.handle.net/10468/18361
dc.language.isoenen
dc.publisherAmerican Chemical Society (ACS)en
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/Pathway Programme::STEM-led/22/PATH-S/10767/IE/SOS-Phosphorus: Sustainable Organic Synthesis with Phosphorus/en
dc.relation.projectinfo:eu-repo/grantAgreement/SFI/Research Infrastructure Programme/21/RI/9705/IE/Fast reaction kinetics in NMR Spectroscopy - FaNS/en
dc.rights© 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.5c04813en
dc.subjectChemical synthesisen
dc.subjectDisulfidesen
dc.subjectOrganophosphorus compoundsen
dc.subjectPiperidinesen
dc.subjectSulfuren
dc.titleIsothioureas as coupling partners in P–S bond formation through cross-dehydrogenative couplingen
dc.typeArticle (peer-reviewed)en
dc.typejournal-articleen
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