Acid-Catalyzed Synthesis of α-Trifluoromethylthiolated Carbonyl Compounds

The α‐trifluoromethylthiolation of carbonyl compounds in soft acidic conditions has been developed. With this method only mono‐trifluoromethylthiolation was selectively observed. Base‐sensitive ketones can then be trifluoromethylthiolated. More sensitive aldehydes are also trifluoromethylthiolated u...

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Bibliographic Details
Published in:European journal of organic chemistry 2015-07, Vol.2015 (21), p.4607-4610
Main Authors: Alazet, Sébastien, Ismalaj, Ermal, Glenadel, Quentin, Le Bars, Didier, Billard, Thierry
Format: Article
Language:English
Subjects:
Biochemistry
Biochemistry, Molecular Biology
Carbonyl compounds
Chemical Sciences
Enols
Fluorine
Life Sciences
Organic chemistry
Trifluoromethanesulfenamide
Trifluoromethylthiolation
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Summary:The α‐trifluoromethylthiolation of carbonyl compounds in soft acidic conditions has been developed. With this method only mono‐trifluoromethylthiolation was selectively observed. Base‐sensitive ketones can then be trifluoromethylthiolated. More sensitive aldehydes are also trifluoromethylthiolated under these conditions with good yields. This work provides a new route towards the synthesis of various valuable trifluoromethylthiolated molecules. One reagent, two possibilities: Complementary to previously described base‐catalyzed reactions, α‐trifluoromethylthiolations of carbonyl compounds were realized in soft acidic conditions with a second generation trifluoromethanesulfenamide. Different selectivities were then observed. With this new strategy, all types of CF3S‐carbonyl compounds can be synthesized by starting from the same reagent.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201500710