A robust methodology for the synthesis of phosphorothioates, phosphinothioates and phosphonothioates

dc.contributor.authorJones, David J.
dc.contributor.authorO'Leary, Eileen M.
dc.contributor.authorO'Sullivan, Timothy P.
dc.contributor.funderUniversity College Corken
dc.date.accessioned2020-04-27T14:35:29Z
dc.date.available2020-04-27T14:35:29Z
dc.date.issued2020-03-04
dc.date.updated2020-04-27T14:23:17Z
dc.description.abstractA robust methodology for the synthesis of phosphorothioates, phosphinothioates and phosphonothioates, including those bearing low molecular weight S‐alkyl side‐chains, is presented. Application of the “caesium effect” in conjunction with the disulfide 3,3’‐dithiobis(propionitrile), which acts as a shelf‐stable sulfur source, avoids recourse to malodorous alkanethiols and toxic P−Cl precursors. A diverse range of sulfur‐containing organophosphorus targets, including phosphorus‐based heterocycles, may be prepared in consistently high yields. This chemistry also provides ready access to the corresponding DBU salts which are potential substrates for Pd‐catalysed coupling reactions.en
dc.description.sponsorshipUniversity College Cork (UCC Strategic Research Fund PhD Scholarship)en
dc.description.statusPeer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationJones, D. J., O'Leary, E. M., O'Sullivan, T. P. (2020) 'A Robust Methodology for the Synthesis of Phosphorothioates, Phosphinothioates and Phosphonothioates', Advanced Synthesis and Catalysis, doi: 10.1002/adsc.202000059en
dc.identifier.doi10.1002/adsc.202000059en
dc.identifier.endpage7en
dc.identifier.issn1615-4150
dc.identifier.journaltitleAdvanced Synthesis and Catalysisen
dc.identifier.startpage1en
dc.identifier.urihttps://hdl.handle.net/10468/9872
dc.language.isoenen
dc.publisherWileyen
dc.rights© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the peer reviewed version of the following article: Jones, D.J., O'Leary, E.M. and O'Sullivan, T.P. (2020), A Robust Methodology for the Synthesis of Phosphorothioates, Phosphinothioates and Phosphonothioates. Adv. Synth. Catal., which has been published in final form at https://doi.org/10.1002/adsc.202000059. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.en
dc.subjectCaesium effecten
dc.subjectPhosphinothioatesen
dc.subjectPhosphonothioatesen
dc.subjectPhosphorothioatesen
dc.subjectPhosphorusen
dc.subjectSulfuren
dc.titleA robust methodology for the synthesis of phosphorothioates, phosphinothioates and phosphonothioatesen
dc.typeArticle (peer-reviewed)en
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