Iron-catalysed Suzuki coupling? A cautionary tale

During an investigation on a reported iron-catalysed Suzuki reaction, we uncovered how little palladium contamination is required to generate positive results. In our hands, Fe(II) or (III) pyridine complexes show no activity in Suzuki biaryl cross-coupling reactions, except in one irreproducible in...

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Bibliographic Details
Published in:Tetrahedron letters 2009-11, Vol.50 (45), p.6110-6111
Main Authors: Bedford, Robin B., Nakamura, Masaharu, Gower, Nicholas J., Haddow, Mairi F., Hall, Mark A., Huwe, Michael, Hashimoto, Tohru, Okopie, Rukeme A.
Format: Article
Language:English
Subjects:
Biaryls
Iron catalysts
Pyridine ligands
Suzuki cross-coupling
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Summary:During an investigation on a reported iron-catalysed Suzuki reaction, we uncovered how little palladium contamination is required to generate positive results. In our hands, Fe(II) or (III) pyridine complexes show no activity in Suzuki biaryl cross-coupling reactions, except in one irreproducible instance when complete conversion was observed. A comparison with palladium acetate under the same conditions showed that complete conversion can be obtained in a S:C ratio of 1,000,000:1 and therefore extreme caution must be exercised to prevent ‘false-positives’ arising from trace Pd-contaminants.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.08.022