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Synfacts 2009(4): 0464-0464
DOI: 10.1055/s-0028-1087864
DOI: 10.1055/s-0028-1087864
Polymer-Supported Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Olefination of Aldehydes Using PEG-Supported Iron(II) Porphyrin
S. L. Jain, J. K. Joseph, F. E. Kühn*, O. Reiser*
Universität Regensburg and Technische Universität München, Germany; Indian Institute of Petroleum, Dehradun, India
Further Information
Publication History
Publication Date:
23 March 2009 (online)
Significance
Poly(ethylene glycol)-immobilized Fe(II) porphyrin was prepared and found to promote the olefination of aldehydes. Thus, tetra-4-tert-butylphenylporphyrin was metalated with Fe(OAc)2 to give complex 2. Etherification of MeOPEG5000 3 with propargyl bromide followed by cycloaddition of the resulting polymer 4 with azidoporphyrin 2 afforded PEG-immobilized Fe(II) porphyrin 5. Olefination of benzaldehyde with ethyl diazoacetate 7 was carried out with Ph3P in the presence of solid-supported Fe(II) porphyrin 5 to give ethyl cinnamate 8a in 96% yield.