α,α-Difluoro-α-phenylsulfanyl-α-trimethylsilylmethane as “CF2−” synthetic building block for the preparation of gem-difluoromethylenated cyclopentanols

A general strategy for the preparation of gem-difluoromethylenated cyclopentanols has been demonstrated; it involves sequential fluoride-catalyzed nucleophilic addition of α,α-difluoro-α-phenylsulfanyl-α-trimethylsilylmethane (PhSCF2SiMe3; 1) to homoallyl ketones followed by intramolecular radical cyclization.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► α,α-Difluoro-α-phenylsulfanyl-α-trimethylsilylmethane as gem-difluoromethylene building block. ► Fluoride-catalyzed nucleophilic addition of α,α-difluoro-α-phenylsulfanyl-α-trimethylsilylmethane to homoallyl ketones. ► Preparation of gem-difluoromethylenated cyclopentanols.