Citation: Ullah Aziz, Zhang Sheng, Bao Ming. Facile Synthesis of β-Methylstyrenes via Pd/TsOH-Catalyzed Isomerization of Allylbenzenes[J]. Chinese Journal of Organic Chemistry, ;2017, 37(5): 1278-1283. doi: 10.6023/cjoc201702031 shu

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

State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023

Corresponding author: Zhang Sheng, shengzhang@dlut.edu.cn
Received Date: 21 February 2017
Revised Date: 13 April 2017

Fund Project: and the China Postdoctoral Science Foundation 2016M590226Project supported by the National Natural Sciences Foundation of China 21602026

Figures(1)

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.
- isomerization,
- allylbenzene,
- β-methylstyrene,
- palladium-catalyzed
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