Chinese Journal of Organic Chemistry >
Facile Synthesis of β-Methylstyrenes via Pd/TsOH-Catalyzed Isomerization of Allylbenzenes
Received date: 2017-02-21
Revised date: 2017-04-13
Online published: 2017-04-27
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
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
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