Regioselective Synthetic Approach to Higher Alkenes from Lower Alkenes with Sulfoxides in the Fe³⁺/H₂O₂ System via Direct Alkylation or Arylation of the Csp²-H Bond on the C=C Bond of Alkenes

Miao-Dong Su, Yu-Feng Liu, Zhi-Wen Nie, Tong-Lin Yang, Zhong-Zhong Cao, Hui Li, Wei-Ping Luo, Qiang Liu* and Can-Cheng Guo*

*College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China, Email: fqiangliuqq.com, ccguohnu.edu.cn

M.-D. Su, Y.-F. Liu, Z.-W. Nie, T.-L. Yang, Z.-Z. Cao, H. Li, W.-P. Luo, Q. Liu, C.-C. Guo, J. Org. Chem., 2022, 87, 7022-7032.

DOI: 10.1021/acs.joc.2c00047

---

see article for more reactions

Abstract

The combination of Fe³⁺/H₂O₂ mediates a regioselective alkylation or arylation of alkenes with sulfoxides as alkyl or aryl reagents. Higher alkenes including di-, tri-, and tetra-substituted products were regioselectively synthesized. Both aliphatic and aromatic alkenes could participate in this reaction.

see article for more examples

proposed mechanism

---

---

Key Words

alkylation of alkenes, hydrogen peroxide

---

ID: J42-Y2022