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- Title
S-((Phenylsulfonyl)difluoromethyl)thiophenium Salts: Carbon-Selective Electrophilic Difluoromethylation of β-Ketoesters, β-Diketones, and Dicyanoalkylidenes.
- Authors
Wang, Xin; Liu, Guokai; Xu, Xiu‐Hua; Shibata, Naoyuki; Tokunaga, Etsuko; Shibata, Norio
- Abstract
S-((Phenylsulfonyl)difluoromethyl)thiophenium salts were designed and prepared by a triflic acid catalyzed intramolecular cyclization of ortho-ethynyl aryldifluoromethyl sulfanes. The thiophenium salts were found to be efficient as electrophilic difluoromehtylating reagents for introduction of a CF2H group to sp3-hybridized carbon nucleophiles such as of β-ketoesters and dicyanoalkylidenes. The (phenylsulfonyl)difluoromethyl group can be readily transformed into CF2H under mild reaction conditions. Enantioselective electrophilic difluoromethylation was also achieved in the presence of bis(cinchona) alkaloids.
- Subjects
ORGANONITROGEN compounds; KETONES; RING formation (Chemistry); NUCLEOPHILES; ORGANIC chemistry
- Publication
Angewandte Chemie International Edition, 2014, Vol 53, Issue 7, p1827
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201309875