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

Yewen Fang*, Li Zhang, Jinjian Li, Xiaoping Jin*, Meijuan Yuan, Ruifeng Li*, Rong Wu and Jianghua Fang

*Ningbo University of Technology, Ningbo 315016; Taiyuan University of Technology, Taiyuan 030024; Zhejiang Pharmaceutical College, Ningbo 315100, China, Email: fangnbut.edu.cn, xiaop.jingmail.com, rflityut.edu.cn

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

DOI: 10.1021/ol503518h

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Abstract

α-Phosphonovinyl tosylates can be coupled efficiently with a range of arylboronic acids to provide α-arylethenylphosphonates. The unprecedented procedure exhibits excellent functional group tolerance, giving the terminal vinylphosphonates in good to excellent isolated yields under mild reaction conditions.

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

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

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Key Words

alkenylation, phosphonates, Suzuki coupling

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ID: J54-Y2015