Metal-free, photoredox-catalyzed aromatization-driven deconstructive functionalization of spiro-dihydroquinazolinones with α-CF alkenes

• Published in: Chemical communications (Cambridge, England) England), 2024-07, Vol.6 (62), p.895-898
• Main Authors: Zhang, Jin-Hua, Miao, Hong-Jie, Li, Jia-Yi, Li, Wenke, Ma, Pengchen, Duan, Xin-Hua, Guo, Li-Na
• Format: Article
• ISSN: 1359-7345; 1364-548X
• DOI: 10.1039/d4cc02868f

Metal-free, photoredox-catalyzed aromatization-driven deconstructive functionalization of spiro-dihydroquinazolinones with α-CF 3 alkenes is presented. The readily available spiro-dihydroquinazolinones reacted efficiently with α-CF 3 alkenes during photocatalysis to give the gem -difluoroallylated and the CF 3 -containing quinazolin-4(3 H )-ones in good yields with excellent chemoselectivity. The selectivity depends on the electron effect of substituents in α-CF 3 alkenes. A wide range of four-, five-, six-, seven-, eight- and twelve-membered spiro-dihydroquinazolinones were compatible with this transformation. The protocol is also characterized by the mild and redox-neutral reaction conditions, good functional group compatibility and excellent atom economy. Mechanistic studies revealed that the reaction proceeds via a radical pathway. Metal-free, photoredox-catalyzed aromatization-driven deconstructive functionalization of spiro-dihydroquinazolinones with α-CF 3 alkenes is achieved with high chemoselectivity. Mechanistic studies suggest a radical pathway for this cascade reaction.