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Copper(I) Zeolites as Heterogeneous and Ligand‐Free Catalysts: [3+2] Cycloaddition of Azomethine Imines
Author(s) -
Keller Murielle,
Sido Abdelkarim Sani Souna,
Pale Patrick,
Sommer Jean
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200802191
Subject(s) - cycloaddition , regioselectivity , catalysis , chemistry , ligand (biochemistry) , combinatorial chemistry , copper , pyrazolone , organic chemistry , biochemistry , receptor
Abstract Clicking in zeolites : Copper(I)‐exchanged zeolites proved to be practical and efficient catalysts for the cycloaddition of azomethine imines with alkynes, providing a convenient access to N , N ‐bicyclic pyrazolidinone derivatives (see scheme). With high regioselectivity, 100 % atom economy, and convenient product isolation, this heterogeneously catalyzed version of the Dorn cycloaddition corresponds to click‐chemistry criteria.Copper(I)‐exchanged zeolites were used as heterogeneous ligand‐free catalysts for [3+2] cycloaddition of azomethine ylides, which allows versatile, efficient, and highly regioselective synthesis of pyrazolone derivatives. These cheap and easy‐to‐prepare catalysts exhibit wide scope and compatibility with functional groups. They are very simple to use, easy to remove (by simple filtration), and recyclable (up to six times without loss of activity).