Visible-Light-Induced, Organophotocatalytic Di- and Trifluoromethylative C–H Annulation Strategy for the Sustainable Synthesis of 5-(Fluoromethyl)-12H-quinolino[2,1-b]quinazolin-12-ones

Herein, we disclose a visible-light-induced, oxidative di- and trifluoromethylative annulation strategy with 3-(2-(ethynyl)phenyl)quinazolinones for the sustainable synthesis of new classes of biologically active N-heteroaromatics, i.e., 5-(fluoromethyl)-12H-quinolino[2,1-b]quinazolin-12-ones using 4CzIPN as organophotoredox catalyst and CF2HSO2Na or CF3SO2Na as the -CF2H or -CF3 source, respectively. This organophotocatalytic strategy features several notable advantages such as a metal-free protocol, oxygen as an oxidant, mild reaction conditions, and straightforward scalability. Mechanistic studies revealed a radical pathway involving the reductive quenching of the photocatalyst by the fluoromethyl source.