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Synfacts 2006(10): 1076-1076
DOI: 10.1055/s-2006-949289
DOI: 10.1055/s-2006-949289
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York
Catch and Release of Homogeneous Catalysts for Recycling
B. W. T. Gruijters, M. A. C. Broeren, F. L. van Delft, R. P. Sijbesma, P. H. H. Hermkens, F. P. J. T. Rutjes*
Radboud University Nijmegen, Eindhoven University of Technology and Organon N. V., Oss, The Netherlands
Further Information
Publication History
Publication Date:
21 September 2006 (online)
Significance
A new method for recovering and reusing homogeneous catalysts was developed based on reversible hydrogen bonding of the catalysts and a resin-supported scavenger. Thus, the [3+2] cycloaddition of 1 and 2 (1 equiv) was performed with a homogeneous ureido[1H]pyrimidinone (UPy)-tagged catalyst, (Upy-phen)CuPPh3Br, with PPh3 in MeCN at room temperature for 16 h. After an aqueous work-up, the crude product was treated with an ArgoPore resin-supported-UPy 5 in CHCl3. The catalyst was scavenged via hydrogen bonding with 5 to give the complex (Upy-phen)CuPPh3Br·5 in 98.3%. After the catalyst was removed by filtration, the product 3 was isolated in >99% yield.