A robust methodology for the synthesis of phosphorothioates, phosphinothioates and phosphonothioates
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Date
2020-03-04
Authors
Jones, David J.
O'Leary, Eileen M.
O'Sullivan, Timothy P.
Journal Title
Journal ISSN
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Publisher
Wiley
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Abstract
A 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.
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Keywords
Caesium effect , Phosphinothioates , Phosphonothioates , Phosphorothioates , Phosphorus , Sulfur
Citation
Jones, 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.202000059
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© 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.