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Direct Vinylation and Difluorovinylation of Arylboronic Acids Using Vinyl- and 2,2-Difluorovinyl Tosylates via the Suzuki-Miyaura Cross Coupling

Thomas M. Gøgsig, Lina S. Søbjerg, Anders T. Lindhardt (neé Hansen), Kim L. Jensen and Troels Skrydstrup

*The Center for Insoluble Protein Structures (inSPIN), Department of Chemistry and the Interdisciplinary Nanoscience Center, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark, Email: tschem.au.dk

T. M. Gøgsig, L. S. Søbjerg, A. T. Lindhardt (neé Hansen), K. L. Jensen, T. Skrydstrup, J. Org. Chem., 2008, 73, 3404-3410.

DOI: 10.1021/jo7027097 (free Supporting Information)


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Abstract

A Pd(0)-catalyzed Suzuki-Miyaura coupling reaction of aryl boronic acids with vinyl tosylate provides access to styrene derivatives in good yields. The easily accessible vinyl tosylate represents a stable and less toxic alternative to the vinyl halides and the triflate/nonaflate derivatives. Furthermore, this methodology was expanded using the similar and also readily available 2,2-difluorovinyl tosylate.

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Key Words

Suzuki Coupling, Vinylation


ID: J42-Y2008-1120