Metal-Free Direct Dehydroxytri­fluoromethylthiolation of Alcohols via the Umpolung Reactivity of Trifluoromethanesulfenamides

A direct dehydroxytrifluoromethylthiolation of alcohols with trifluoromethanesulfenamide has been described. This method, based on the original umpolung reactivity of trifluoromethanesulfenamides, proposes a direct “OH‐SCF3 exchange” under mild and, more especially, metal‐free conditions. OH ↔ SCF3...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2016-04, Vol.2016 (11), p.1955-1957
Main Authors: Glenadel, Quentin, Tlili, Anis, Billard, Thierry
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Biochemistry
Biochemistry, Molecular Biology
Chemical Sciences
Dehydroxytrifluoromethylthiolation
Fluorine
Life Sciences
Nucleophilic substitution
Organic chemistry
Trifluoromethylthiolation
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Summary:A direct dehydroxytrifluoromethylthiolation of alcohols with trifluoromethanesulfenamide has been described. This method, based on the original umpolung reactivity of trifluoromethanesulfenamides, proposes a direct “OH‐SCF3 exchange” under mild and, more especially, metal‐free conditions. OH ↔ SCF3 exchange. Direct transformation of alcohols into CF3S molecules can be performed with trifluoromethanesulfenamide under mild and metal‐free conditions. This dehydroxytrifluoromethylthiolation reaction is compatible with various alcohols.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201600197