Room temperature C–O bond cleavage of vinyl cyclic synthons via a metallaphotoredox approach

Abstract

Herein, we report visible-light induced C–O bond cleavage of vinyl-appended cyclic synthons via a Co(II)-photoredox dual catalytic approach operating at room temperature. This methodology exhibits a broad scope and is capable of accessing linear as well as branched allyl arenes simply by tuning the ring size of the cyclic motifs, in a mild and environmentally friendly protocol. Mechanistic studies unveil an interesting aspect of the reaction pathway involving a challenging homolytic cleavage of the Co(III)–O bond, 1,5-HAT of an unstable Co(II)-organometallic intermediate, and the key roles of O₂ and the photocatalyst. The successful removal of the directing group further adds an important dimension to the methodology.