Cu‐Catalyzed Formal Addition of Aliphatic C(sp3)−H Bonds to Alkenes via Phenyl Radical Involved Intermolecular HAT

Abstract A copper catalyzed aerobic formal addition of aliphatic C( sp 3)−H bonds to alkenes via a phenyl radical mediated intermolecular HAT process is reported herein, in which the phenylhydrazine not only acts as a HAT reagent precursor, but also as a hydrogen atom donor. This reaction affords an alternative method for the direct formal addition of aliphatic C( sp 3)−H bonds to alkenes utilizing air as the radical initiator without additional reductants at ambient temperature. A variety of alkanes and electron‐deficient alkenes are successfully incorporated, furnishing a series of aliphatic C( sp 3)−H formal addition products in 20–93% yield. Preliminary mechanistic studies show that the 2‐tetrahydrofuranyl and phenyl radical are formed in this reaction.