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Paper | Regular issue | Vol 63, No. 2, 2004, pp.297-308
Published online, 8th December, 2003
DOI: 10.3987/COM-03-9921
Etherificaiton of Heterocyclic Compounds by Nucleophilic Aromatic Substitutions under Green Chemistry Conditions

Matthieu Lloung, André Loupy,* Sylvain Marque, and Alain Petit

*Laboratoire des Réactions Sélectives sur Supports, ICMMO, CNRS UMR 8615, Université de Paris-Sud, Bâtiment 410, 91405 Orsay Cedex, France

Abstract

Solid-liquid phase transfer catalysis coupled with microwave irradiation was shown to be an efficient method for SNAr reaction of halogenated quinoline and pyridine with alkoxides and phenoxides. Whereas for phenoxylation there is no need for any solvent, the addition of small amount of non-polar solvent is necessary during methoxylation for accurate monitoring of temperatures. Yields and conditions involved here constitute a noticeable improvement over classical methods within the frame of Green Chemistry. Specific MW effects were evidenced for phenoxylation and interpreted in terms of late position of the transition state along the reaction coordinates.