Etherification of heterocyclic compounds by nucleophilic aromatic substitutions under green chemistry conditions

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 so...

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Bibliographic Details
Published inHeterocycles Vol. 63; no. 2; pp. 297 - 308
Main Authors Lloung, M, Loupy, A, Marque, S, Petit, A
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.02.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HALIDES
PHASE
ACTIVATION
HALOPYRIDINES
ACIDS
MICROWAVE
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Summary: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.
ISSN:0385-5414
1881-0942
DOI:10.3987/com-03-9921