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

Author:
Grounds, Helen, Ermanis, Kristaps, Newgas, Sophie A., Porter, Michael J.
Source:
Journal of organic chemistry 2017 v.82 no.23 pp. 12735-12739
ISSN:
1520-6904
Subject:
alcohols, chemical reactions, chemical structure, organic chemistry
Abstract:
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.
Agid:
5864497