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

Helen Grounds, Kristaps Ermanis, Sophie A. Newgas and Michael J. Porter*

*Department of Chemistry, University College London, Christopher Ingold Building, 20 Gordon Street, London WC1H 0AJ, U.K., Email:

H. Grounds, K. Ermanis, S. A. Newgas, M. J. Porter, J. Org. Chem., 2017, 82, 12735-12739.

DOI: 10.1021/acs.joc.7b01657

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The use of the iminium salt prepared from N,N-dimethylthioformamide and Meerwein's salt enables a direct and rapid conversion of primary and secondary alcohols to the corresponding phosphorothiolates in good yields. 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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proposed mechanism

Key Words


ID: J42-Y2017