Stereoselective synthesis of α-fluoroacrylonitriles through organocatalytic cyanation of gem-difluoroalkenes and TMSCN

An organocatalytic cyanation reaction of gem-difluoroalkenes was developed. Under the catalysis of 10 mol% DBU, gem-difluoroalkenes undergo nucleophilic addition-β-elimination reaction with trimethylsilyl cyanide to provide α-fluoroacrylonitriles in 50%-98% yields with excellent Z/E selectivity.