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Umpolung trifluoromethylthiolation of alcohols

Herein we develop a metal-free umpolung dehydroxytrifluoromethylthiolation of alcohols with commercially available PPh 3 and N -trifluoromethylthiophthalimide within 30 minutes. This protocol shows excellent functional group tolerance and high regioselectivity. The dehydroxytrifluoromethylthiolation...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-11, Vol.21 (43), p.8663-8666
Main Authors: Yang, Ye, Ma, Jiemin, Zhang, Jiaxiang, Cai, Hu, Xu, Wentao
Format: Article
Language:English
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Summary:Herein we develop a metal-free umpolung dehydroxytrifluoromethylthiolation of alcohols with commercially available PPh 3 and N -trifluoromethylthiophthalimide within 30 minutes. This protocol shows excellent functional group tolerance and high regioselectivity. The dehydroxytrifluoromethylthiolation of a series of natural products and drugs further demonstrates its practicality. Preliminary mechanistic studies suggest that PPh 3 is responsible for deoxygenation and the key trifluoromethylthiophosphonium ion may be hydrolyzed by H 2 O in solvent. A metal-free umpolung dehydroxytrifluoromethylthiolation of alcohols enables late-stage functionalization of complex alcohols.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01535a