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Radical C(sp3)-H Heck-type Reaction of N-Alkoxybenzimidoyl Chlorides with Styrenes to Construct Alkenols.

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We report the first radical C(sp3)-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… Click to show full abstract

We report the first radical C(sp3)-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(sp3)-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.

Keywords: alkoxybenzimidoyl chlorides; heck type; sp3 heck; type reaction

Journal Title: Organic letters
Year Published: 2022

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