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P=S Bond Formation

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Various α,β-unsaturated phosphine sulfides were prepared in goods yields from the parent α,β-unsaturated phosphine oxides with Lawesson's reagent. The reaction offers a broad substrate scope and tolerates various functional groups.
X.-L. Wang, J.-X. Chen, X.-S. Jia, L. Yin, Synthesis, 2020, 52, 141-149.


A stereoselective hydrophosphination reaction of alkynes with diphenylphosphane has been developed. The reaction is mediated by a cobalt catalyst and butyllithium.
H. Ohmiya, H. Yorimitsu, K. Oshima, Angew. Chem. Int. Ed., 2005, 44, 2368-2370.


For the synthesis of thiophosphinic acids, two major approaches were selected: (1) the Stec reaction of phosphorus amides with carbon disulfide; and (2) the one-pot synthesis of thiophosphorus acids from H-phosphinates, an organometallic nucleophile, and quenching with elemental sulfur. An application to the preparation of a potential chiral phosphorus organocatalyst is also reported.
K. R. Winters, J.-L. Montchamp, J. Org. Chem., 2020, 85, 14545-14558.