Nucleophilic difluoromethylenation of aldehydes and ketones using diethyl difluoro(trimethylsilyl)methylphosphonate

A new nucleophilic difluoromethylenation of aldehydes and ketones using diethyl difluoro(trimethylsilyl)methylphosphonate (1) has been achieved. The reactive carbanion species were generated under mild reaction conditions with a catalytic amount of initiator. This methodology was compatible with non-enolizable and in some cases with enolizable aldehydes and ketones and provided a straightforward access to phosphates of syn and anti 2,2-difluoro-1,3-diols.

Direct nucleophilic introduction of CF2 group to aldehydes and ketones starting from diethyl difluoro(trimethylsilyl)methylphosphonate was achieved. Phosphates of syn and anti 2,2-difluoro-1,3-diols were produced in one reaction sequence and under mild conditions using catalytic amount of fluoride initiator.Figure optionsDownload as PowerPoint slide