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

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(sp(2))-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(sp(2))-H and activated or unactivated aliphatic C(sp(3))-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.

Automated summary

A one-step protocol for desulfonylative allylation of C-H bonds using TBADT as a photo-hydrogen atom transfer catalyst is demonstrated. This method shows good functional group tolerance and can be applied for allylation of aldehydes and alkanes.