Intermolecular Trifluoromethyl-Hydrazination of Alkenes Enabled by Organic Photoredox Catalysis

• DOI: 10.1021/acs.orglett.0c00287
• Publication Date: 2020-02-14T12:51:16Z
• Authors: Peng Wang; Songsong Zhu; Dengfu Lu; Yuefa Gong
• Keywords: Trifluoromethylation; Photoredox catalysis; Hydrazine (antidepressant)

A metal-free and redox-neutral trifluoromethyl-hydrazination method of alkenes is described. With a commercially available photocatalyst low-cost reagents, both conjugated isolated could be converted to β-trifluoromethyl hydrazines in good excellent yields. The versatile hydrazine group can either used for heterocycle synthesis or cleaved afford corresponding amine. Mechanistic studies suggested this reaction goes through radical addition cascade pathway, featuring fast irreversible trifluoromethylation relatively slow hydrazination step.