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

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

Volume: 15 Issue: 8

Author(s): Xu Shen, Ping Liu*, Yan Liu*Bin Dai

Affiliation:

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

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

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

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.

Cite this article as:

Shen Xu , Liu Ping *, Liu Yan *, Dai Bin , Synthesis of 1,2-Diarylethylenes by Pd-Catalyzed One-Pot Reaction of Benzyl Halides, Tosylhydrazide, and Aryl Aldehydes, Letters in Organic Chemistry 2018; 15 (8) . https://dx.doi.org/10.2174/1570178615666171222163927