A three component 1,3-difunctionalization of vinyl diazo esters enabled by a cobalt catalyzed C-H activation/carbene migratory insertion.

We report herein, a modular, regioselective 1,3-oxyarylation of vinyl diazo esters a Co-catalyzed C-H activation/carbene migratory insertion cascade. The transformation involves the formation of C-C and C-O bonds in a one-pot fashion and displays a broad substrate scope with respect to both, vinyl diazo esters as well as benzamides. The coupled products were subjected to hydrogenation to access elusive allyl alcohol scaffolds.

A switch to vinylogous reactivity of vinyl diazo esters for the C-H allylation of benzamides by merging cobalt and photoredox catalysis.

Herein, a vinylogous reactivity of vinyl diazo esters in the C-H bond allylation of benzamides has been developed by coalescing cobalt and photoredox catalysis C-H activation/allyl carbene migratory insertion. A close relationship between the high valent cobalt catalyst and the photocatalyst has been found to be crucial for this reactivity. The reaction uses oxygen as the sole oxidant and produces benign nitrogen as the only by-product.