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Synfacts 2006(5): 0517-0517  
DOI: 10.1055/s-2006-934407
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Solid-Supported Copper Catalysts for Atom-Transfer Radical Cyclizations

Contributor(s): Yasuhiro Uozumi, Masahiro Kimura
A. J. Clark*, J. V. Geden, S. Thom
University of Warwick, Coventry and AstraZeneca Research and Development, Loughborough, UK
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Publikationsverlauf

Publikationsdatum:
21. April 2006 (online)

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Significance

The solid-supported pyridine­methanimine (PMI) and polyamine [N,N,N′,N′,N′′-pentamethyldiethylenetriamine (PMDETA), N,N,N,N′,N′-tetraethyldiethylene-triamine ­(TEDETA), and tris(N,N-2-dimethylamino)ethyl­amine (Me6-Tren)] ligands were prepared and used for the copper-catalyzed atom-transfer radical cyclizations. For example, the copper complex of JandaJel-supported PMI ligand 6 catalyzed the cyclization of trichloroacetamide 1 at room temperature to give a cyclized product 2 in a quantitative yield. The 5-endo radical cyclization of 3 by use of JandaJel-supported TEDETA ligand 7 also proceeded via a β-scission step to afford cyclized products 4 and 5 in a quantitative yield.