Synfacts 2007(1): 0083-0083  
DOI: 10.1055/s-2006-955698
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Reduction of Oxygen Functionalities to Alkanes with Alkylsilanes

Contributor(s): Paul Knochel, Andrei Gavryushin
R. D. Nimmagadda, C. McRae*
Macquarie University, Sydney, Australia
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Publikationsverlauf

Publikationsdatum:
15. Dezember 2006 (online)

Significance

Despite the vast number of methods reported for the reduction of oxygen functionalities like ketones, aldehydes and various types of alcohols to the corresponding alkanes, there is a lack of a general, universally suitable protocol for such a transformation. Besides, most of the known procedures also lead to the reduction of C=C double bonds. The method reported herein is free of these drawbacks. It uses commercially available silanes as reducing agents in a very practical, operationally simple protocol. A broad variety of substrates can be reduced without isomerization or migration of double bonds even in the case of conjugated enones.