Silicon polypodands: a new class of efficient solid–liquid phase-transfer catalysts

Silicon polypodands 1– 7 were found to be powerful complexing agents of alkali metal salts, even in low polarity media (chlorobenzene) and hence very efficient phase-transfer catalysts. Their catalytic activity was measured in typical anion-promoted reactions under solid–liquid phase-transfer cataly...

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Bibliographic Details
Published in:Tetrahedron 2004-10, Vol.60 (44), p.10111-10115
Main Authors: Maia, Angelamaria, Landini, Dario, Leska, Boguslawa, Schroeder, Grzegorz
Format: Article
Language:English
Subjects:
Complexing agents
Phase-transfer catalysts
Silicon polypodands
Solid–liquid phase-transfer catalyzed reactions
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Summary:Silicon polypodands 1– 7 were found to be powerful complexing agents of alkali metal salts, even in low polarity media (chlorobenzene) and hence very efficient phase-transfer catalysts. Their catalytic activity was measured in typical anion-promoted reactions under solid–liquid phase-transfer catalysis (SL-PTC) conditions. It is mainly determined by the complexing ability of the ligand, increasing with the number of silicon atoms and binding sites. Comparison with traditional phase-transfer catalysts showed that these polypodands are better catalysts not only than open-chain PEG400Me 2 and TRIDENT, but even than more sophisticated macrocyclic polyethers such as DCH18C6. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.06.049