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Synthesis of 1,2-Diarylethylenes by Pd-Catalyzed One-Pot Reaction of Benzyl Halides, Tosylhydrazide, and Aryl Aldehydes

[ Vol. 15 , Issue. 8 ]

Author(s):

Xu Shen, Ping Liu*, Yan Liu* and Bin Dai   Pages 709 - 715 ( 7 )

Abstract:


Background: Substituted olefins are versatile functional groups and intermediates in chemistry, medicine, electronics, and optics and materials science fields because of their unique properties. One important class of substituted olefins 1,2-diarylethylenes have attracted considerable attention due to their presence in both natural products and pharmacologically active substances.

Methods: In this paper, we developed a one-pot two-step coupling reaction of aryl aldehydes, tosylhydrazide with benzyl halides by using inexpensive Pd(PPh3)4 as catalyst, leading to a variety of 1,2- diphenylethenes derivatives with moderate to good yields.

Results: The desired 1,2-diarylethylenes were obtained in 46-96% yields via Pd(0)-catalyzed one-pot reaction of benzyl halides, tosylhydrazide, and aryl aldehydes.

Conclusion: The catalytic system presented here enables the use of easily accessible starting materials and good functional group tolerance.

Keywords:

1, 2-Diarylethylene, Pd-catalyzed, N-tosylhydrazones, aromatic aldehydes, benzyl halides, one-pot reaction.

Affiliation:

School of Chemistry and Chemical Engineering, The Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi City, School of Chemistry and Chemical Engineering, The Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi City, School of Chemistry and Chemical Engineering, The Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi City, School of Chemistry and Chemical Engineering, the Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi City

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