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Synfacts 2011(5): 0522-0522  
DOI: 10.1055/s-0030-1259822
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Suzuki Coupling of Monofluorovinyl Tosylates

Contributor(s): Mark Lautens, Stephen G. Newman
H. Zhang, C.-B. Zhou, Q.-Y. Chen, J.-C. Xiao*, R. Hong*
Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
15 April 2011 (online)

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Significance

Incorporation of fluorine into molecules has many effects, such as altering solubility, conformation, and reactivity. In the preparation of simple vinyl fluorides, controlling E/Z selectivity can be remarkably difficult. The authors prepare a range of vinyl fluorides starting from monofluoro­vinyl tosylate building blocks. Suzuki coupling of the tosylate group gives the arylated products in good yield and stereoselectivity.