Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 155, Issue -, Pages 52-58Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2013.05.015
Keywords
(Phenylsulfonyl)difluoromethylation; Difluoromethylation; Nucleophilic fluoroalkylation; Hydrofluorocarbons; Aldehydes; Alcohols
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Funding
- National Basic Research Program of China [2012CB821600, 2012CB215500]
- National Natural Science Foundation of China [20825209, 21202189]
- Chinese Academy of Sciences
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The reactions between carbonyl compounds and PhSO2CF2H using substoichiometric amount of base in situ generated from N(TMS)(3) and catalytic amount of Me4NF have been investigated. It is found that both enolizable and non-enolizable aldehydes are suitable substrates to undergo nucleophilic difluoro(phenylsulfonyl)methylation. Compared to the previously reported trifluoromethylation of carbonyls with CF3H under the similar reaction conditions, the unique reactivity of PhSO2CF2H is attributed to its higher acidity than CF3H and the reversibility of its addition reaction with ketones under basic conditions. (C) 2013 Elsevier B.V. All rights reserved.
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