Ketone-derived 2,3-dihydroquinazolinones in N -heteroarene C-H alkylation via C-C bond scission under oxidative metal catalysis.

A silver-catalysed oxidative sp 2 C-H alkylation of N -heteroarenes with ketone-derived 2,3-dihydroquinazolinones at room temperature is developed. The combination of a metal catalyst and perdisulfate oxidant promotes the rarely explored thermal activation of pre-aromatic 2,3-dihydroquinazolinone to generate an alkyl radical, supported by mechanistic studies. In addition to the broad scope, good functionality tolerance, late stage functionalization of APIs, and synthesis of a novel Papaverine analogue, the utilization of an N -heteroarene C-H bond and ketone as a non-trivial alkyl radical source represents the salient feature of this method.