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Alkoxide-Catalyzed Reduction of Ketones with Pinacolborane

Ian P. Query, Phillip A. Squier, Emily M. Larson, Nicholas A. Isley and Timothy B. Clark*

*Department of Chemistry, Western Washington University, 516 High Street, Bellingham, Washington 98225, United States, Email: clarktsandiego.edu

I. P. Query, P. A. Squier, E. M. Larson, N. A. Isley, T. B. Clark, J. Org. Chem., 2011, 76, 6452-6456.

DOI: 10.1021/jo201142g (free Supporting Information)


Abstract

The reduction of ketones with pinacolborane is catalyzed by NaOt-Bu at ambient temperature. The reaction is high yielding and general, providing complete conversion of aryl and dialkyl ketones. The active hydride source is the trialkoxyborohydride, which is believed to be present in low concentration under the reaction conditions.

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Key Words

Reduction of Ketones, Pinacolborane


ID: J42-Y2011-2220