4.4 Article

Facile route to benzils from aldehydes via NHC-catalyzed benzoin condensation under metal-free conditions

Journal

TETRAHEDRON LETTERS
Volume 51, Issue 13, Pages 1786-1789

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.01.103

Keywords

N-Heterocyclic carbene; Benzil; Benzoin; Oxidation; Organocatalyst

Funding

  1. Japan Society for the Promotion of Science (JSPS) [20550103]
  2. Grants-in-Aid for Scientific Research [20550103] Funding Source: KAKEN

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A simple and efficient one-pot procedure for the synthesis of alpha-diketones from aldehydes via benzoin condensation under the influence of a catalytic amount of azolium salt combined with DBU has been developed. Thus, aldehyde was allowed to react with the azolium salt/DBU catalytic system at room temperature, and then the reaction mixture was heated to 70 degrees C under air atmosphere to afford the corresponding 1,2-diketone in good yield. This would be an efficient alternative method of synthesizing alpha-diketones from alclehydes under metal-free conditions. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.

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