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Pure Appl. Chem., 2009, Vol. 81, No. 11, pp. 2001-2012

Published online 2009-10-30

Onium-tagged Ru complexes as universal catalysts for olefin metathesis reactions in various media

Łukasz Gułajski1*, Marc Mauduit2 and Karol Grela1,3

1 Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland
2 “Sciences Chimiques de Rennes”, École Nationale Supérieure de Chimie de Rennes CNRS, UMR 6226 Université Européenne de Bretagne Avenue du Général Leclerc, CS 50837 35708 Rennes Cedex 7, France
3 Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland

Abstract: Polar olefin metathesis catalysts bearing a pendant electron-withdrawing (EWG) onium group are reviewed. The presence of this group not only activates the catalysts electronically, but renders them more hydrophilic. Catalysts can, therefore, be efficiently used not only in traditional media such as methylene chloride and toluene, but also in technical-grade alcohols, alcohol–water mixtures, and in neat water. In addition, some onium-tagged catalysts can act as inisurfs (initiator + surfactant molecules), promoting metathesis under heterogeneous aqueous conditions. Finally, some of these catalysts can be used in ionic liquids. Various ring-closing-, cross- and enyne metathesis reactions were conducted with these catalysts.