Regioselective and Diastereoselective Halofunctionalization of Alkenes Promoted by Organophotocatalytic Solar Catalysis

A visible-light metal-free photocatalytic regioselective and enantioselective alkene halofunctionalization reaction under mild conditions is reported. Various terminal and internal alkenes were transformed to their alpha-halogenated and alpha,beta- dibrominated derivatives in good to excellent yields within reaction time as short as 5 min. Water can be used as the green nucleophile and solvent in the halohydroxylation and halo oxidation reactions. Different types of products can be obtained by adjusting the reaction conditions. In addition, sunlight is proved to produce products with similar yields, representing a practical example of solar synthesis and providing an opportunity for solar energy utilization.

Automated summary

A visible-light metal-free photocatalytic regioselective and enantioselective alkene halofunctionalization reaction under mild conditions is described. Various terminal and internal alkenes could be transformed to α-halogenated and α,β-dibrominated derivatives with good to excellent yields in as short as 5 min reaction time. Water serves as the green nucleophile and solvent in halohydroxylation and halo oxidation reactions. Different types of products can be obtained by adjusting the reaction conditions. Moreover, sunlight demonstrates the ability to produce similar yields, showcasing a practical example of solar synthesis and offering an opportunity for solar energy utilization.