Conversion of Alcohols to Phosphorothiolates Using a Thioiminium Salt as Coupling Agent
2017
Grounds, Helen | Ermanis, Kristaps | Newgas, Sophie A. | Porter, Michael J.
We report a method for the direct and rapid conversion of primary and secondary alcohols to the corresponding phosphorothiolates in yields ranging from 64% to 97%, using as a coupling agent the iminium salt prepared from N,N-dimethylthioformamide and Meerwein’s salt. Selective reaction of primary alcohols in the presence of secondary alcohols is possible. The reaction of secondary alcohols proceeds stereospecifically with inversion of configuration.
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