Aerobic Coupling of Organophosphonium Salts with Alkenes: Catalyst‐Free C(<i>sp</i><sup>3</sup>)−C(<i>sp</i><sup>2</sup>) Bond Formation
Meng‐Meng Guo, Gan‐Qi Qin, Xinyu Jiang, Hao Xu, Mengtao Ma, Zhi‐Liang Shen, Xue‐Qiang Chu
Abstract
Abstract 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.
Topics & Concepts
ChemistryCatalysisPhosphoniumSubstrate (aquarium)Triple bondDouble bondMedicinal chemistryOxidative coupling of methaneCarbon fibersStereochemistryOrganic chemistryGeologyComposite numberMaterials scienceOceanographyComposite materialCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesRadical Photochemical Reactions