Direct Access to Ketones from Aldehydes via Rhodium-Catalyzed Cross-Coupling Reaction with Potassium Trifluoro(organo)borates

Mathieu Pucheault, Sylvain Darses,* and Jean-Pierre Genet*;
Laboratoire de Synthse Slective Organique (UMR 7573, CNRS), Ecole Nationale Suprieure de Chimie de Paris, 11 rue P&M Curie, 75231 Paris Cedex 05, France
J. Am. Chem. Soc., 2004, 126 (47), pp 15356–15357
DOI: 10.1021/ja044749b
Publication Date (Web): November 4, 2004
Copyright © 2004 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, darses@ext.jussieu.fr, ; , genet@ext.jussieu.fr

Abstract

Abstract Image

A direct cross-coupling reaction of aromatic aldehydes with potassium trifluoro(organo)borates afforded ketones in high yields and under mild conditions in the presence of a rhodium catalyst and acetone. This new reaction, involving a formal aldehyde C−H bond activation, is believed to proceed via a Heck-type mechanism followed by hydride transfer to acetone.

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History

  • Published In Issue December 01, 2004
  • Received August 31, 2004

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