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Synlett 2015; 26(07): 980-984
DOI: 10.1055/s-0034-1380326
letter
© Georg Thieme Verlag Stuttgart · New York

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

Yewen Fang*
a   School of Chemical Engineering, Ningbo University of Technology, No.89 Cuibai Road, Ningbo 315016, P. R. of China   eMail: fang@nbut.edu.cn
,
Li Zhang
b   College of Chemistry and Chemical Engineering, Taiyuan University of Technology, No. 79 West Yingze Street, Taiyuan 030024, P. R. of China
,
Xiaoping Jin*
c   Department of Biology and Pharmaceutical Sciences, Zhejiang Pharmaceutical College, No. 888 Yinxian Avenue East, Ningbo 315100, P. R. of China
,
Jinjian Li
a   School of Chemical Engineering, Ningbo University of Technology, No.89 Cuibai Road, Ningbo 315016, P. R. of China   eMail: fang@nbut.edu.cn
,
Meijuan Yuan
b   College of Chemistry and Chemical Engineering, Taiyuan University of Technology, No. 79 West Yingze Street, Taiyuan 030024, P. R. of China
,
Ruifeng Li*
b   College of Chemistry and Chemical Engineering, Taiyuan University of Technology, No. 79 West Yingze Street, Taiyuan 030024, P. R. of China
,
Haoqi Gao
a   School of Chemical Engineering, Ningbo University of Technology, No.89 Cuibai Road, Ningbo 315016, P. R. of China   eMail: fang@nbut.edu.cn
,
Jianghua Fang
a   School of Chemical Engineering, Ningbo University of Technology, No.89 Cuibai Road, Ningbo 315016, P. R. of China   eMail: fang@nbut.edu.cn
,
Yuyan Liu
a   School of Chemical Engineering, Ningbo University of Technology, No.89 Cuibai Road, Ningbo 315016, P. R. of China   eMail: fang@nbut.edu.cn
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Publikationsverlauf

Received: 30. Dezember 2014

Accepted: 19. Januar 2015

Publikationsdatum:
20. Februar 2015 (online)

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Abstract

An efficient new synthetic route to (1-arylvinyl)phosphonates is presented. A wide range of (1-arylvinyl)phosphonates were prepared in good to excellent yields (79–99%) by using a palladium(II) acetate–organophosphine catalyst system. The protocol can be effectively scaled up without deleterious effects. The use of a (1-chloro­vinyl)phosphonate as the electrophilic coupling partner was demonstrated for the first time.

Key words

cross-coupling - phosphonates - palladium - catalysis - arylation

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380326.
  • Supporting Information
 

  • References and Notes

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