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Synfacts 2011(11): 1230-1230  
DOI: 10.1055/s-0031-1289201
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

γ-Selective Cross-Coupling of Allylic Silanolate Salts

Contributor(s): Paul Knochel, Thomas Kunz
S. E. Denmark*, N. S. Werner
University of Illinois at Urbana-Champaign, USA
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Publication History

Publication Date:
19 October 2011 (online)

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Significance

In this work, a γ-selective, palladium-catalyzed cross-coupling of sodium (Z)-2-butenyldiethylsilanolate is disclosed. The silanolate salt is easily prepared and configurationally stable. High yields are obtained for electron-poor, -rich, sterically demanding, and heteroaromatic bromides.