Organophotoredox-Catalyzed Oxidative C(sp2 )-H Alkylation of N-Heteroarenes with Dihydroquinazolinones by C-C Cleavage

We report a visible-light-mediated, organophotoredox-catalyzed, C(sp(2))-H alkylation of N-heteroarenes with dihydroquinazolines, prepared from aliphatic ketones, under oxidative conditions. This protocol represents a metal-free approach to the effective construction of C-C bonds through a Minisci-type reaction, formally activating the native C-H bond of the N-heteroarene and an a-C-C bond of a readily available ketone. The mild nature of this method accommodates a wide variety of N-heteroarenes and ketones, tolerating a wide range of functional groups.

Automated summary

We present a metal-free visible-light-mediated C(sp(2))-H alkylation of N-heteroarenes with dihydroquinazolines derived from aliphatic ketones under oxidative conditions. This strategy enables the construction of C-C bonds through a Minisci-type reaction, activating the native C-H bond of the N-heteroarene and an α-C-C bond of a readily available ketone. The versatility of this mild method allows for the use of various N-heteroarenes and ketones, with tolerance towards a broad range of functional groups.