Aerobic Coupling of Organophosphonium Salts with Alkenes: Catalyst-Free C(sp(3))-C(sp(2)) Bond Formation

An aerobic coupling of benzhydryl phosphonium salts with simple alkenes for accessing trisubstituted olefins is developed under metal-free, catalyst-free, and additive-free conditions. New C(sp(3))-C(sp(2)) bond is constructed via the C-P and C-H bond functionalization by synergistically using O-2 as a green oxidant and DMSO as a promoter. The method also distinguishes itself by its broad substrate scope and synthetic potential. Particularly, the use of 1,3,5-trimethoxybenzene fragment in the resulting products as a carbon-based leaving group for further transformations is proved to be feasible.

Automated summary

This study presents a metal-free, catalyst-free, and additive-free aerobic coupling reaction of benzhydryl phosphonium salts with simple alkenes to access trisubstituted olefins. The C(sp(3))-C(sp(2)) bond is formed through the functionalization of C-P and C-H bonds using O-2 as a green oxidant and DMSO as a promoter. The method demonstrates a broad substrate scope and synthetic potential, with the 1,3,5-trimethoxybenzene fragment in the resulting products proving to be feasible for further transformations.