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Synfacts 2009(8): 0894-0894
DOI: 10.1055/s-0029-1217478
DOI: 10.1055/s-0029-1217478
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Ionic Ethane-1,2-diboron Species as a Synthetically Useful Dianion Equivalent
G. A. Molander*, D. L. Sandrock
University of Pennsylvania, Philadelphia, USA
Further Information
Publication History
Publication Date:
23 July 2009 (online)
Significance
The authors report the addition of 9-borabicyclo[3.3.1]nonane to potassium vinyltrifluoroborate yielding a 1,2-dianion equivalent C2 species. Subsequent Suzuki-Miyaura cross-coupling to a number of functionalized arenes, heteroarenes and olefins using the palladium acetate/DavePhos, X-Phos and RuPhos systems affords ethylene-linked biaryls or olefinated arenes, respectively. A broad range of functional groups are tolerated and the products can be isolated in very good yields.