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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:,

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

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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.

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proposed mechanism

Key Words

alkylation of alkenes, hydrogen peroxide

ID: J42-Y2022