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Monofluorovinyl Tosylate: A Useful Building Block for the Synthesis of Terminal Vinyl Monofluorides via Suzuki-Miyaura Coupling

He Zhang, Chang-Bing Zhou, Qing-Yun Chen, Ji-Chang Xiao* and Ran Hong*

*Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China, Email: jchxiaosioc.ac.cn, rhongsioc.ac.cn

H. Zhang, C.-B. Zhou, Q.-Y. Chen, J.-C. Xiao, R. Hong, Org. Lett., 2011, 13, 560-563.

DOI: 10.1021/ol102645g (free Supporting Information)



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Abstract

Monofluorovinyl tosylate is a practical vinyl fluoride building block to couple with various arylboronic acids in the presence of a palladium catalyst. A high stereoselectivity in the synthesis of 2-aryl-1-fluoroethene derivatives was achieved. This approach is also applicable to the synthesis of 2,2-diaryl-1-fluoroethenes in good yields.


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Key Words

Vinyl Fluorides, Arenes, Suzuki Coupling


ID: J54-Y2011-0280