Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (5): 1278-1283.DOI: 10.6023/cjoc201702031 Previous Articles     Next Articles



乌拉·阿齐兹, 张胜, 包明   

  1. 大连理工大学精细化工国家重点实验室 大连 116023
  • 收稿日期:2017-02-21 修回日期:2017-04-13 发布日期:2017-04-27
  • 通讯作者: 张胜
  • 基金资助:


Facile Synthesis of β-Methylstyrenes via Pd/TsOH-Catalyzed Isomerization of Allylbenzenes

Ullah Aziz, Zhang Sheng, Bao Ming   

  1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023
  • Received:2017-02-21 Revised:2017-04-13 Published:2017-04-27
  • Contact: 10.6023/cjoc201702031
  • Supported by:

    Project supported by the National Natural Sciences Foundation of China (No. 21602026) and the China Postdoctoral Science Foundation (No. 2016M590226).

Convenient and efficient protocol for isomerization of allylbenzenes into corresponding β-methylstyrenes has been developed. Different acids, solvents and catalysts have been investigated. Pd(TFA)2 and TsOH·H2O as catalysts in dichloromethane at room temperature under air for 12 h were selected as standard conditions for exploring the substrate scope. Allylbenzenes containing electron-donating groups and electron-withdrawing groups were working under the optimized condition, and β-methylstyrene products were obtained in the yields of 65%~90%. The reaction mechanism was proposed according to the deuterated experiment.

Key words: isomerization, allylbenzene, β-methylstyrene, palladium-catalyzed