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A palladium-catalyzed anti-Markovnikov hydroalkylation of β,β-difluorinated homoallylic alcohols with alkylzinc reagents has been developed. This method affords a wide range of synthetically useful gem-difluorinated compounds with good functional group compatibility.

A one-pot nickel-catalyzed allylation of aromatic aldehydes with α-halo-β,β-difluoropropene-containing compounds promoted by ZnEt(2) under mild conditions was described. The reaction displays moderate to good regio- and diastereoselectivity, tolerates a wide range of functional groups, and provides an efficient method for the synthesis of γ-fluorinated homoallylic alcohols.

We report the first example of iron-catalyzed cross-coupling of α-halo-β,β-difluoroethylene-containing compounds with arylzinc reagents using TMEDA and dppp as coligands. The reaction affords a wide range of functional group tolerant gem-difluoromethylenated compounds in moderate to good yields. The facile dehalodefluorination of α-halo-β,β-difluoroethylene-containing compounds upon treatment of reductive metal reagents was mostly inhibited. Mechanistic studies indicated that the cross-coupling reaction could involve a single-electron-transfer process.