Color-coded ligands: Tracking the catalyst using highly pigmented porphyrazine ligands in biphasic reactions

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Journal Article
Organometallics, 2014, 33 (24), pp. 7023 - 7026
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© 2014 American Chemical Society. We demonstrate the concept that highly colored imidazolium porphyrazine ligands and complexes may be useful for visualizing the location of a catalyst and/or ligand. This was analytically demonstrated by the application of UV-vis spectrophotometry to detect the ligand and ICP-OES spectroscopy for quantification of the Pd in the biphasic systems. In the first instance, a toluene/water system was used, in which the complex and ligand preferred the organic phase. Water-soluble substrates were made to react under these conditions by employing the complexes as catalysts in Heck and Suzuki C-C bond forming reactions. In the second instance, an ionic liquid containing biphasic mixture was used, in which the ligand/catalyst was retained in the ionic liquid. Catalyst recycling experiments were met with limited success.
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