Visible light-induced direct α C–H functionalization of alcohols

Considering the synthetic value of introducing active alcoholic hydroxyl group, developing C–H functionalization of alcohols is of significance. Herein, we present a photochemical method that under visible light irradiation, selectfluor can effectively promote the oxidative cross-coupling between alcohols and heteroarenes without the external photocatalysis, achieving the selective α sp3 C–H arylation of alcohol, even in the presence of ether. The N-F activation of selectfluor under blue LEDs irradiation is evidenced by electron paramagnetic resonance (EPR) study, which is the key process for the oxidative activation of α sp3 C–H alcohols. The observed reactivity may have significant implications for chemical transformations. Alcohols are very useful building blocks in organic synthesis, however C–H functionaliztion in presence of free –OH groups is highly challenging. Here, the authors report a selective visible light-promoted α-functionalization of free alcohols with heteroarenes mediated by Selectofluor.