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

Meng-Meng Guo,^a Gan-Qi Qin,^a Xin-Yu Jiang,^a Hao Xu,^a* Mengtao Ma,^b Zhi-Liang Shen,^a* and Xue-Qiang Chu^a*

^a Technical Institute of Fluorochemistry, Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, People’s Republic of China. E-mail: xuhao@njtech.edu.cn; ias_zlshen@njtech.edu.cn; xueqiangchu@njtech.edu.cn.

^b Department of Chemistry and Materials Science, College of Science, Nanjing Forestry University, Nanjing 210037, People’s Republic of China.

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(sp³)−C(sp²) bond is constructed via the C−P and C−H bond functionalization by synergistically using O₂ 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.

Advanced Synthesis & Catalysis 2023, 365, 1871–1876. (Impact factor: 5.4)

论文链接：https://onlinelibrary.wiley.com/doi/10.1002/adsc.202300259