Wang Peng, Zhu Songsong, Lu Dengfu, Gong Yuefa
School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan, Hubei 430074, China.
Org Lett. 2020 Mar 6;22(5):1924-1928. doi: 10.1021/acs.orglett.0c00287. Epub 2020 Feb 14.
A metal-free and redox-neutral trifluoromethyl-hydrazination method of alkenes is described. With a commercially available photocatalyst and low-cost reagents, both conjugated and isolated alkenes could be converted to β-trifluoromethyl hydrazines in good to excellent yields. The versatile hydrazine group can be either used for heterocycle synthesis or cleaved to afford a corresponding amine. Mechanistic studies suggested this reaction goes through a radical addition cascade pathway, featuring a fast and irreversible trifluoromethylation and a relatively slow radical hydrazination step.
