Decatungstate-Mediated C(sp(3))-H Heteroarylation via Radical-Polar Crossover in Batch and Flow

Photocatalytic hydrogen atom transfer is a very powerful strategy for the regioselective C(sp(3))-H functionalization of organic molecules. Herein, we report on the unprecedented combination of decatungstate hydrogen atom transfer photocatalysis with the oxidative radical-polar crossover concept to access the direct net-oxidative C(sp(3))-H heteroarylation. The present methodology demonstrates a high functional group tolerance (40 examples) and is scalable when using continuous-flow reactor technology. The developed protocol is also amenable to the late-stage functionalization of biologically relevant molecules such as stanozolol, (-)-ambroxide, podophyllotoxin, and dideoxyribose.