Photolysis of alkylcobaloximes in the presence of activated alkenes results in both β-H elimination and alkyl–alkenyl cross coupling. A proposed mechanism predicts that buildup of the persistent radical ⋅CoII- (dmgH)2py as the reactions proceed enhances β-H elimination, lowering the yield of cross coupling. Scavengers of ⋅CoII(dmgH)2py suppress β-H elimination and enhance cross coupling, presumably by lowering the concentration of ⋅CoII(dmgH)2py. These data provide support for the proposed reaction mechanism and illustrate how a persistent radical can control product distributions in an organometallic radical reaction.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry