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Aminocarbonyl Group Containing Hoveyda−Grubbs-Type Complexes: Synthesis and Activity in Olefin Metathesis Transformations

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Diane Rix^†, Fréderic Caijo^†, Isabelle Laurent^†, Fabien Boeda^‡, Hervé Clavier ^‡, Steven P. Nolan ^‡ and Marc Mauduit ^†

“Sciences Chimiques de Rennes” UMR 6226 CNRS-Equipe Chimie Organique et Supramoléculaire-Ecole Nationale Supérieure de Chimie de Rennes, Av. du Général Leclerc, 35700 Rennes, France, and Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans, 16. 43007 Tarragona, Spain

J. Org. Chem., 2008, 73 (11), pp 4225–4228

DOI: 10.1021/jo800203d

Publication Date (Web): May 7, 2008

, †

“Sciences Chimiques de Rennes” UMR 6226 CNRS-Equipe Chimie Organique et Supramoléculaire-Ecole Nationale Supérieure de Chimie de Rennes.

, ‡

Institute of Chemical Research of Catalonia.

Abstract

Three novel “boomerang” precatalysts bearing different aminocarbonyl functions are reported. Comparative kinetic studies show that this functional group allows for a control of the catalytic activity in metathesis transformations. The scope of the more active catalyst is investigated and shows a good tolerance to various substrates in ring-closing metathesis, enyne metathesis, and cross metathesis. ICP-MS analyses illustrate the good affinity of this catalyst for silica gel, as levels of Ru contamination lower than 6 ppm are detected in the final products.

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