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Synfacts 2006(3): 0261-0261
DOI: 10.1055/s-2006-932011
DOI: 10.1055/s-2006-932011
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York
Air-Assisted Oxidative Coupling of Grignard Reagents with Olefins
Y. Nobe, K. Arayama, H. Urabe*
Tokyo Institute of Technology, Yokohama, Japan
Further Information
Publication History
Publication Date:
21 February 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.