Issue 41, 2021

Lewis base-free thiophosphonium ion: a cationic sulfur atom transfer reagent

Abstract

Phosphorus(V) sulfide and Lawesson's reagent are commonly used thionating reagents which are considered to operate after dissociation into highly reactive dithiophosphorane fragments. We report the synthesis and properties of a monomeric thiophosphonium ion [R2P[double bond, length as m-dash]S]+. The highly electrophilic species reacts with carbonyls in oxo-for-sulfido exchange reactions at room temperature and undergoes phosphorus–chalcogen bond metathesis reactions with phosphine chalcogenides.

Graphical abstract: Lewis base-free thiophosphonium ion: a cationic sulfur atom transfer reagent

Supplementary files

Article information

Article type
Communication
Submitted
09 Mar 2021
Accepted
16 Apr 2021
First published
16 Apr 2021
This article is Open Access
Creative Commons BY license

Chem. Commun., 2021,57, 5043-5046

Lewis base-free thiophosphonium ion: a cationic sulfur atom transfer reagent

P. Löwe, T. Witteler and F. Dielmann, Chem. Commun., 2021, 57, 5043 DOI: 10.1039/D1CC01273H

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