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Synfacts 2008(6): 0631-0631  
DOI: 10.1055/s-2008-1072779
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

α-Arylation of Enaminones Using Organotrifluoroborates

Contributor(s): Paul Knochel, Andrei Gavryushin
H. Ge, M. J. Niphakis, G. I. Georg*
University of Kansas, Lawrence and University of Minnesota, Minneapolis, USA
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Publication History

Publication Date:
21 May 2008 (online)

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Significance

Structures possessing a 3-aryl­piperidine and similar heterocyclic scaffolds are known to display a broad spectrum of biological activity. Cyclic enaminones are useful precursors for that type of compounds. This method of a enaminone arylation competes favorably with the previously known halogenation-cross-coupling sequence, as it proceeds in a single step. A variety of enaminones and aryltrifluoroborates can be successfully involved in this reaction. Many functional groups including halides are tolerated.