Expedient Synthesis of Terminal Vinylphosphonates by Palladium-Catalyzed C-C Cross-Coupling Reactions of (1-Halovinyl)phosphonates

Yewen Fang*, Li Zhang, Xiaoping Jin, Jinjian Li, Meijuan Yuan, Ruifeng Li, Haoqi Gao, Jianghua Fang, Yuyan Liu

*School of Chemical Engineering, Ningbo University of Technology, No.89 Cuibai Road, Ningbo 315016, P. R. of China, Email: fangnbut.edu.cn

Y. Fang, L. Zhang, X. Jin, J. Li, M. Yuan, R. Li, H. Gao, J. Fang, Y. Liu, Synlett, 2015, 26, 980-984.

DOI: 10.1055/s-0034-1380326

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Abstract

The use of a palladium(II) acetate-organophosphine catalyst system enables an efficient coupling of (1-bromovinyl)phosphonates with aryl boronic acids. A wide range of (1-arylvinyl)phosphonates were prepared in very good yields. The protocol can be effectively scaled up and even allows the use of a (1-chloro­vinyl)phosphonate as the electrophilic coupling partner.

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Applications of α-Phosphonovinyl Tosylates in the Synthesis of α-Arylethenylphosphonates via Suzuki-Miyaura Cross-Coupling Reactions

Y. Fang, L. Zhang, J. Li, X. Jin, M. Yuan, R. Li, R. Wu, J. Fang, Org. Lett., 2015, 17, 798-801.

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Key Words

Suzuki cross-coupling, phosphonates, alkenylation, palladium, catalysis, arylation

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ID: J60-Y2015