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

Grounds, H; Ermanis, K; Newgas, SA; Porter, MJ; (2017) Conversion of Alcohols to Phosphorothiolates Using a Thioiminium Salt as Coupling Agent. Journal of Organic Chemistry , 82 (23) pp. 12735-12739. 10.1021/acs.joc.7b01657. Green open access

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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.

Type: Article
Title: Conversion of Alcohols to Phosphorothiolates Using a Thioiminium Salt as Coupling Agent
Open access status: An open access version is available from UCL Discovery
DOI: 10.1021/acs.joc.7b01657
Publisher version: https://doi.org/10.1021/acs.joc.7b01657
Language: English
Additional information: This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html), which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10027743
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