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Synfacts 2009(5): 0547-0547  
DOI: 10.1055/s-0028-1088184
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Cross-Coupling of Silanolates with Aromatic Halides

Contributor(s): Paul Knochel, Andrei Gavryushin
S. E. Denmark*, R. C. Smith, W.-T. T. Chang, J. M. Muhuhi
University of Illinois at Urbana-Champaign, USA
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Publication History

Publication Date:
22 April 2009 (online)

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Significance

In recent years, the cross-coupling of organosilanolates 1 attracted significant attention as an alternative for the Suzuki-Miyaura ­coupling. In this publication, an efficient cross-coupling of a range of aryl- and heteroarylsilanolates with aryl chlorides and bromides under mild conditions is reported. Three general methods for the synthesis of arylsilanolates from the corresponding aryl halides are also presented.