Advanced Fine-Tuning of Grubbs/Hoveyda Olefin Metathesis Catalysts:  A Further Step toward an Optimum Balance between Antinomic Properties

Michał Bieniek,† Robert Bujok,† Maciej Cabaj,†‡ Noël Lugan,§ Guy Lavigne,*§ Dieter Arlt,* and Karol Grela*†;
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland, Faculty of Chemistry, Warsaw University of Technology, Koszykowa 75, 00-662 Warsaw, Poland, Laboratoire de Chimie de Coordination du CNRS, 205 route de Narbonne, 31077 Toulouse Cedex 4, France, and Ligand Chemie GmbH Papenhauser Strausse 10, Lemgo D-32657, Germany
J. Am. Chem. Soc., 2006, 128 (42), pp 13652–13653
DOI: 10.1021/ja063186w
Publication Date (Web): October 4, 2006
Copyright © 2006 American Chemical Society
†

 Polish Academy of Sciences.

,
‡

 Warsaw University of Technology.

,
§

 Laboratoire de Chimie de Coordination du CNRS.

,
*

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

,

 Ligand Chemie GmbH.

, lavigne@lcc-toulouse.fr; prof.arlt@t-online.de, ; , grela@icho.edu.pl

Abstract

Abstract Image

A 95% yield in the cross metathesis of acrylonitrile with a model olefin is achieved at 25 °C with only 3 mol % of the new air-stable ruthenium catalyst 1f shown in the enclosed structural diagram. Even more remarkable are the performances of its boosted version 1g incorporating an electron-withdrawing group. Both these new enhanced versions of Hoveyda catalyst are readily available from Grubbs second generation precatalyst upon reaction with a styrenyl ether the end group of which has been functionalized by an ester function. The latter acts as a weakly coordinating ligand allowing to reach a desirable balance between antinomic properties such as the catalyst's stability, a high activity for challenging substrates, and a high initiation rate.

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History

  • Published In Issue October 25, 2006
  • Received May 6, 2006

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