A copper catalyzed aerobic formal addition of aliphatic C(sp3)−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(sp3)−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(sp3)−H formal addition products in 20–93% yield. Preliminary mechanistic studies show that the 2-tetrahydrofuranyl and phenyl radical are formed in this reaction.

本文报道了通过苯基介导的分子间HAT过程，铜催化脂肪族C( sp 3)-H键与烯烃的有氧形式加成，其中苯肼不仅充当HAT试剂前体，而且充当氢原子供体。该反应提供了另一种在环境温度下利用空气作为自由基引发剂将脂肪族C( sp 3)-H键直接正式加成到烯烃上的方法，无需额外的还原剂。多种烷烃和缺电子烯烃被成功结合，以 20-93% 的产率提供一系列脂肪族 C( sp 3)−H 形式加成产物。初步机理研究表明，该反应中形成2-四氢呋喃基和苯基自由基。