1606148-89-3Relevant academic research and scientific papers
S-((Phenylsulfonyl)difluoromethyl)thiophenium salts: Carbon-selective electrophilic difluoromethylation of β-ketoesters, β-diketones, and dicyanoalkylidenes
Wang, Xin,Liu, Guokai,Xu, Xiu-Hua,Shibeta, Naoyuki,Tokunaga, Etsuko,Shibata, Norio
, p. 1827 - 1831 (2014/03/21)
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 CF 2H 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. S and F join forces: The title salts were designed and prepared by a triflic acid catalyzed intramolecular cyclization of ortho-ethynyl aryldifluoromethyl sulfanes. The salts 1 were efficient as electrophilic difluoromethylating reagents for introducing a CF2H group to sp3-hybridized carbon nucleophiles. Enantioselective electrophilic difluoromethylation was also investigated. DBU=1,8-diazabicyclo[5.4.0]undec-7-ene, Tf=trifluoromethanesulfonyl. Copyright
