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

Abstract

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