3 years ago

Conversion of Alcohols to Phosphorothiolates Using a Thioiminium Salt as Coupling Agent

Conversion of Alcohols to Phosphorothiolates Using a Thioiminium Salt as Coupling Agent
Helen Grounds, Kristaps Ermanis, Michael J. Porter, Sophie A. Newgas
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01657

DOI: 10.1021/acs.joc.7b01657

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