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Visible light induced regioselective C5 halogenation of 8-aminoquinolines with 1,3-dihalo-5,5-dimethylhydantoin in continuous flow
- Shu, Quan, Li, Yaming, Liu, Tong, Zhang, Siyu, Jiang, Linlin, Jin, Kun, Zhang, Rong, Duan, Chunying
- Tetrahedron 2019 v.75 no.26 pp. 3636-3642
- air, ambient temperature, aminoquinolines, chemical reactions, light, moieties, regioselectivity
- An efficient and convenient method for remote C5 halogenation of 8-aminoquinoline derivatives was developed in continuous flow at room temperature. This method employed inexpensive 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichlro-5,5-dimethylhydantoin (DCDMH) as halogenation reagents and visible light to catalyze the reaction. The reaction is scalable to gram-scale and proceeded with air and moisture tolerance, good functional group compatibility, and outstanding site selectivity, providing a new pathway for C5 halogenation of 8-aminoquinolines.