Synfacts 2006(3): 0261-0261  
DOI: 10.1055/s-2006-932011
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Air-Assisted Oxidative Coupling of Grignard Reagents with Olefins

Contributor(s): Paul Knochel, Andrei Gavryushin
Y. Nobe, K. Arayama, H. Urabe*
Tokyo Institute of Technology, Yokohama, Japan
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Publikationsverlauf

Publikationsdatum:
21. Februar 2006 (online)

Significance

This work represents a novel protocol for the addition of Grignard reagents to alkenes, with subsequent oxidation of the alcohol. Among the common Grignard reagents, tert-alkyl-, aryl-, and vinylmagnesium halides react well. The reaction follows a classical radical addition mechanism. Therefore, mixtures of products, especially in reactions with dienes, are sometimes obtained. Styrenes, dienes and enynes are suitable substrates for this reaction. The overall process offers an easy functionalization of alkenes to form corresponding alcohols.