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Synfacts 2007(8): 0854-0854  
DOI: 10.1055/s-2007-968738
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Stereoselectivity in Cross-Coupling of α-Bromo Sulfoxides and Arylboronic Acids

Contributor(s): Paul Knochel, Andrei Gavryushin
N. Rodríguez, C. Ramírez de Arellano, G. Asensio*, M. Medio-Simón
Universidad de Valencia, Spain
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Publication History

Publication Date:
24 July 2007 (online)

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Significance

This is the first report concerning a mechanistic study of still rather uncommon Csp 3-Csp 2 cross-coupling reactions. The whole process was shown to proceed with inversion of the configuration, which takes place on the palladium oxidative addition step. Since enantiopure aryl sulf­oxides are readily available, this method has also a significant synthetic utility for the preparation of various chiral target molecules.