Aerobic Coupling of Organophosphonium Salts with Alkenes: Catalyst‐Free C(sp³)−C(sp²) Bond Formation

Abstract

An aerobic coupling of benzhydryl phosphonium salts with simple alkenes for accessing trisubstituted olefins is developed under metalfree, catalyst-free, and additive-free conditions. New C(sp 3 )À C(sp 2 ) bond is constructed via the CÀ P and CÀ 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.

Synthesis and Functionalization of Thiophosphonium Salts: A Divergent Approach to Access Thioether, Thioester, and Dithioester Derivatives

“… 8 In this method, benzhydrylamines, benzhydrylthioethers, and triarylmethanes, structural motifs that are present in many pharmaceuticals and agrochemicals, are respectively readily accessed. 8 Furthermore, Chu 12 , 13 and co-workers have developed an efficient metal-free difluoroalkylation reaction of these organophosphonium salts ( VII ) with difluoroenol silyl ethers ( Scheme 1 A). 12 , 13 …”

“… 8 Furthermore, Chu 12 , 13 and co-workers have developed an efficient metal-free difluoroalkylation reaction of these organophosphonium salts ( VII ) with difluoroenol silyl ethers ( Scheme 1 A). 12 , 13 …”