title: N-Difluoromethylthiophthalimide: A Shelf-Stable, Electrophilic Reagent for Difluoromethylthiolation.
abstract: A new, electrophilic difluoromethylthiolating reagent N-difluoromethylthiophthalimide 3 was developed. Reagent 3 can be readily synthesized in four steps from easily available starting materials phthalimide and TMSCF2H. N-difluoromethylthiophthalimide 3 is a powerful electrophilic difluoromethylthiolating reagent that allows the difluoromethylthiolation of a wide range of nucleophiles including aryl/vinyl boronic acids, alkynes, amines, thiols, β-ketoesters, and oxindoles and electron-rich heteroarenes such as indole, pyrrole, 1H-pyrrolo[2,3-b]pyridine, imidazo[1,2-a]pyridine, aminothiazole, isoxazole, and pyrazole under mild conditions.
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, People's Republic of China.
authors.forename: Dianhu
authors.initials: D
authors.lastname: Zhu
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, People's Republic of China.
authors.forename: Yang
authors.initials: Y
authors.lastname: Gu
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, People's Republic of China.
authors.forename: Long
authors.initials: L
authors.lastname: Lu
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, People's Republic of China.
authors.forename: Qilong
authors.initials: Q
authors.lastname: Shen
mesh_terms: D000480:Alkynes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D004583:Electrons; D007211:Indoles / Q000737:chemistry; D000078183:Oxindoles; D010797:Phthalimides / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: D000480:Alkynes; D000588:Amines; D001897:Boronic Acids; D007211:Indoles; C000608469:N-difluoromethylthiophthalimide; D000078183:Oxindoles; D010797:Phthalimides; D013438:Sulfhydryl Compounds; C022960:2-oxindole; C037431:phthalimide; D003300:Copper