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Issue 7, 2019
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Robust and electron deficient oxidovanadium(IV) porphyrin catalysts for selective epoxidation and oxidative bromination reactions in aqueous media

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Abstract

meso-Tetrakis(3,5-dimethoxyphenyl)porphyrinatooxidovanadium (1) and β-octabromo-meso-tetrakis(2,6-dibromo-3,5-dimethoxyphenyl)porphyrinatooxidovanadium (2) were synthesized in excellent yields. The synthesized oxidovanadium(IV) porphyrin complexes were characterized by various spectroscopic methods such as UV-Vis, FT-IR, EPR and MALDI-TOF mass spectrometry, as well as by single crystal X-ray crystallography. The acetonitrile coordinated porphyrin 1 is relatively planar whereas 2 is highly nonplanar as shown by their crystal structures and also by electrochemical studies. Selective epoxidation studies of alkenes were successfully carried out in CH3CN/H2O as the solvent mixture at ambient temperature resulting in very high TOF numbers (12 227–14 347 h−1 for 2) even with low catalyst loadings. Remarkably, 2 biomimics the vanadium bromoperoxidase (VBrPO) enzyme with extremely high TOF values (83 333–87 719 h−1) for the oxidative bromination of thymol and some other phenols. Both the catalysts were successfully recovered at the end of the reactions, indicating their viability and industrial applicability.

Graphical abstract: Robust and electron deficient oxidovanadium(iv) porphyrin catalysts for selective epoxidation and oxidative bromination reactions in aqueous media

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Publication details

The article was received on 13 Dec 2018, accepted on 18 Feb 2019 and first published on 21 Feb 2019


Article type: Paper
DOI: 10.1039/C8GC03909G
Green Chem., 2019,21, 1757-1768

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    Robust and electron deficient oxidovanadium(IV) porphyrin catalysts for selective epoxidation and oxidative bromination reactions in aqueous media

    T. A. Dar, B. Uprety, M. Sankar and M. R. Maurya, Green Chem., 2019, 21, 1757
    DOI: 10.1039/C8GC03909G

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