Desilylative Ring-Opening Strategy for Skipped 1,5-Diene Synthesis Under Synergistic Photoredox/Nickel Catalysis

Herein, we report a dual photoredox/nickel-catalyzed alkenylation of aryl cyclopropanes, enabling access to diverse skipped 1,5-dienes. This synergistic strategy proceeds via orbital-controlled formation of a key benzylic radical intermediate, stabilized by the β-silicon effect, thereby expanding the reaction paradigm beyond the conventional nucleophilic activation of aryl cyclopropanes. The protocol provides selective access to 1,5-diene products in moderate to good yields. Mechanistic studies, including radical quenching and control experiments, support a nickel/visible-light-induced radical pathway.