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Evaluation and Development of Methodologies for the Synthesis of Thiophosphinic Acids

Karen R. Winters and Jean-Luc Montchamp*

*Department of Chemistry, Texas Christian University, PO Box 298860, Fort Worth, Texas 76129, United States, Email: j.montchamptcu.edu

K. R. Winters, J.-L. Montchamp, J. Org. Chem., 2020, 85, 14545-14558.

DOI: 10.1021/acs.joc.0c01151 (free Supporting Information)


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Abstract

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.

 

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proposed mechanism



Key Words

thionation


ID: J42-Y2020