Iodine(III)-Mediated Photochemical C-H Azolation

Radical chemistry is an important enabling tool for organic synthesis but can be plagued by the lack of comprehensive polarity and therefore reactivity analysis scheme. Herein we have formulated a systematic radical polarity analysis framework for the projection of radical reactivity patterns. An iodine(III)-mediated photochemical C-H azolation reaction has been envisaged and developed based on the set of empirical guidelines. The synthesis features an environmentally benign reagent, a mild reaction condition, an operationally simple protocol, and a broad substrate scope. The inclusive demonstration of reactivity for ether, thioether, amide, benzylic, and allylic C-H bonds promises synthetic utility in a pervasive range of application settings.