N‑Difluoromethylthiophthalimide: A Shelf-Stable, Electrophilic Reagent for Difluoromethylthiolation

• Published in: Journal of the American Chemical Society Vol. 137; no. 33; pp. 10547 - 10553
• Main Authors: Zhu, Dianhu, Gu, Yang, Lu, Long, Shen, Qilong
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 26-08-2015
• Subjects: Alkynes - chemistry; Amines - chemistry; Boronic Acids - chemistry; Catalysis; Copper - chemistry; Electrons; Indoles - chemistry; Phthalimides - chemistry; Sulfhydryl Compounds - chemistry
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/jacs.5b03170

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.