Efficient synthesis and Suzuki cross-coupling reactions of meso-tetrakis(2,6-dimethyl-4-triflyloxyphenyl)porphyrin |
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Authors: | Julien Taesch Tung T Dang Valérie Heitz |
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Institution: | Laboratoire de Synthèse des Assemblages Moléculaires Multifonctionnels, Institut de Chimie de Strasbourg, CNRS/UMR 7177, 4, rue Blaise Pascal, 67070 Strasbourg Cedex, France |
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Abstract: | An ortho-dimethyl substituted meso-tetrakisarylporphyrin prefunctionalized with triflate groups was prepared in good yield from an accessible 2,6-dimethyl-4-(triflyloxy)benzaldehyde. This porphyrin is an interesting building block, which could directly be engaged in Suzuki cross-coupling reactions, to be further tetra functionalized with 3-pyridyl ligands in yields equal or above 85%. The porphyrin core of the various compounds bearing four remote coordination sites was metalated with zinc(II). The molecular structures of the starting triflate porphyrin derivative and of the zinc(II) porphyrin substituted with four 3-pyridyl groups bearing a protected alcohol were determined using X-ray crystallography. |
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