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Synfacts 2007(4): 0417-0417  
DOI: 10.1055/s-2007-968332
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Suzuki Cross-Coupling of N-Vinylpyridinium and Ammonium Tetrafluoroborates

Contributor(s): Paul Knochel, Andrei Gavryushin
K. R. Buszek*, N. Brown
Kansas State University, Manhattan, University of Kansas, Lawrence and University of Missouri, Kansas City, USA
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Publication History

Publication Date:
23 March 2007 (online)

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Significance

This is a new interesting method for the introduction of a enone moiety into an aryl ring by means of a cross-coupling reaction. The vinyl­pyridinium salts are readily prepared from the corresponding ynones and pyridinium tetrafluoro­borate and are crystalline solids, convenient to handle and store. The reaction proceeds within several minutes under the assistance of microwave heating. Mechanistically, this is the first example of the oxidative insertion of Pd(0) into alkenyl­ammonium bonds.