α,α-Difluoro-α-phenylsulfanyl-α-trimethylsilylmethane as a difluoromethyl building block: A general strategy to α,α-difluoromethyl aryl ketones

• Published in: Journal of fluorine chemistry 2011-11, Vol.132 (11), p.987-990
• Main Authors: Boonkitpattarakul, Kanhokthron, Soorukram, Darunee, Tuchinda, Patoomratana, Reutrakul, Vichai, Pohmakotr, Manat
• Format: Article
• Language: English
• Subjects: α,α-Difluoro-α-phenylsulfanyl-α-trimethylsilylmethane; α,α-Difluoromethyl aryl ketones
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2011.06.036

The synthetic utility of α,α-difluoro-α-phenylsulfanyl-α-trimethylsilylmethane (PhSCF 2SiMe 3) as gem-difluoromethyl building block for the synthesis of α,α-difluoromethyl aryl ketones was described. [Display omitted] ► The synthetic utility of α,α-difluoro-α-phenylsulfanyl-α-trimethylsilylmethane. ► α,α-Difluoromethyl ketones via sulfoxide elimination. ► α,α-Difluoro-α-phenylsulfanyl-α-trimethylsilylmethane as a difluoromethyl building block. The synthetic utility of α,α-difluoro-α-phenylsulfanyl-α-trimethylsilylmethane (PhSCF 2SiMe 3; 1) as a difluoromethyl building block providing a general strategy to α,α-difluoromethyl aryl ketones was demonstrated. Oxidation, by using m-chloroperoxybenzoic acid, of the readily available 1-aryl-2,2-difluoro-2-phenylsulfanyl-1-trimethylsiloxyethanes obtained from fluoride-catalyzed nucleophilic addition of PhSCF 2SiMe 3 with aromatic aldehydes followed by flash vacuum pyrolytic elimination provided α,α-difluoromethyl aryl ketones in moderate overall yields.