Herein, a general protocol for the hydroazolylation of alkenes with N-hydroxyl azoles is reported. These reactions proceed via a phosphoranyl radical that is accessed by photoredox catalysis, followed by radical coupling of the resulting azole radical to the alkenes radical. The key point of this reaction lies in the specific binding between the hydroxy group on N-hydroxyazole and alkyl phosphine. This specificity enables the reaction to overcome the selectivity issues associated with existing hydroazolylation reactions, arising from the conjugation effects of different nitrogen atoms in azole substrates, leading to N1/N2/N3 reaction site selectivity problems. Moreover, this protocol is also applicable to both intramolecular alkenes and external non-terminal alkenes.

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