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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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Published in: | Organic & biomolecular chemistry 2023-11, Vol.21 (43), p.8663-8666 |
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Main Authors: | , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 1477-0520 1477-0539 |
DOI: | 10.1039/d3ob01535a |