Radical C(sp 3 )-H Heck-type Reaction of N -Alkoxybenzimidoyl Chlorides with Styrenes to Construct Alkenols.

We report the first radical C(sp 3 )-H Heck-type reaction of aliphatic alcohols for selective δ- and ε-alkenol synthesis by photoredox catalysis. N -Alkoxybenzimidoyl chlorides are developed as novel alkoxyl radical precursors with tunable redox potentials. Various alkenols can be constructed by the inert C(sp 3 )-H Heck-type reaction of 4-cyano- N -alkoxybenzimidoyl chlorides with styrene derivatives under redox-neutral conditions, which can be performed on the gram scale and can be easily derivatized.