Decatungstate-mediated desulfonylative allylation and diacrylation using aldehydes/alkanes and allylic sulfones

Abstract

Radical-initiated allylation reactions represent a powerful tool for installation of a synthetically useful allyl group for further transformations. In this field, direct allylation of C–H bonds has received considerable attention due to its high atom-efficiency and environmentally benign nature. Despite these advancements, the current strategies still have some limitations, such as the utilization of stoichiometric HAT reagents and excessive amounts of C–H substrates, incompatibility with aldehydic C(sp²)–H bonds, and reliance on dual catalysis or multiple steps. Herein, a one-step protocol for desulfonylative allylation of C–H bonds of aldehydes and alkanes with allyl sulfones using TBADT as a photo-hydrogen atom transfer catalyst is reported. This methodology requires only a single equivalent of C–H substrates and has been applied for the allylation of aldehydic C(sp²)–H and activated or unactivated aliphatic C(sp³)–H with good functional group tolerance. Moreover, this methodology exhibits further application potential for diacrylation of allylic sulfones by slightly adjusting the ratio of reactants, presenting a direct and facile access to highly substituted 1,5-diketones in good to high yields.