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.

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► 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.