Unexpected Formation of Aryl Ketones by Palladium-Catalyzed Coupling of Aryl Bromides with Vinylic Acetates

Mickaël Jean,§ Jacques Renault,§ Philippe Uriac,*§ Marc Capet,† and Pierre van de Weghe*§‡;
EA Substances Lichniques et Photoprotection, Facult de Pharmacie, Universit de Rennes 1, 2 avenue du Professeur Lon Bernard, F-35043 Rennes Cedex, France, Bioprojet-Biotech, 4 rue du Chesnay Beauregard, BP96205, F-35762 Saint-Grgoire, France and Laboratoire de Chimie Organique et Bioorganique associ au CNRS, ENSC-Mu, Universit de Haute Alsace, 3 rue A. Werner, F-68093 Mulhouse Cedex, France
Org. Lett., 2007, 9 (18), pp 3623–3625
DOI: 10.1021/ol7015065
Publication Date (Web): August 1, 2007
Copyright © 2007 American Chemical Society
§

 Faculté de Pharmacie, Université de Rennes 1.

,
*

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

,
†

 Bioprojet-Biotech.

,
‡

 COB, Université de Haute Alsace.

, philippe.uriac@univ-rennes1.fr, ; , pierre.van-de-weghe@univ-rennes1.fr

Abstract

Abstract Image

A palladium-catalyzed coupling reaction of aryl bromides with vinylic acetates in the presence of tributyltin methoxide has been described. Unexpected formation of aryl ketones was obtained. Preliminary mechanistic studies indicated that the reaction proceeded by the addition of the aryl moiety in the coordination sphere of palladium to a ketene.

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History

  • Published In Issue August 30, 2007
  • Received June 25, 2007

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