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Synfacts 2006(9): 0934-0934  
DOI: 10.1055/s-2006-949211
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Reductive Olefination of Aldehydes via Chromium Brook Rearrangement

Contributor(s): Paul Knochel, Andrei Gavryushin
R. Baati, C. Mioskowski*, D. Barma, R. Kache, J. R. Falck*
Université Louis Pasteur de Strasbourg, France and University of Texas, Dallas, USA
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

This paper describes a new interesting method for inter- and intramolecular reductive coupling of aldehydes. The method represents an alternative to the well-known McMurry reaction. A wide variety of substituted benzaldehydes and cinnamaldehyde can be used for this reaction. The double bond geometry of the product is dictated by thermodynamic factors. The presence of functional groups like phenols or halogens does not interfere with the reaction. The synthetic protocol is simple and practical and proceeds at 65 °C within 8-12 h.