Double Allylic Defluorinative Alkylation of 1,1-Bisnucleophiles with (Trifluoromethyl)alkenes: Construction of All-Carbon Quaternary Centers

A double allylic defluorinative alkylation reaction of 1,1-bisnucleophiles with (trifluoromethyl)alkenes is reported that occurs via the exclusively regioselective SN2 reaction. Various aliphatic nitriles, esters, and indolin-2-one derivatives could serve as the 1,1-bisnucleophiles, delivering diverse attractive symmetric gem-difluoroalkene substituted products in high yields via the construction of the all-carbon quaternary centers. Interestingly, the chemoselective SNV reaction between gem-difluoroalkenes and nucleophiles is completely inhibited. The nitrile group might help to stabilize the α-carbanion intermediates.