Dual activation process in a copper(II)oxoisoindoline-catalyzed catechol oxidation

The mononuclear [Cu(3′MePyOIND)2] (3′MePyOINDH: 3-(3′-methyl-2′-pyridylimino)isoindoline-1-one) complex has been prepared and characterized by various techniques such as elemental analysis, IR, UV–vis and ESR spectroscopy. The title compound was suitable as catalyst for the catalytic oxidation of 3,5-di-tert-butylcatechol (3,5-DTBC-H2) to 3,5-di-tert-butyl-1,2-benzoquinone (3,5-DTBQ) (catecholase activity) with dioxygen at ambient condition in good yields. Kinetic measurements revealed first-order dependence on the catalyst and dioxygen concentration and saturation type behavior with respect to the corresponding substrate. It was also found that the complex shows dual effects, acts as a base deprotonating 3,5-DTBC-H2 and also as a redox catalyst, activating O2 during the oxidation reaction.

Graphical abstractMonomeric copper(II) complex Cu(3′MePyOIND)2 was isolated, characterized, and found to be suitable catalysts for the catalytic oxidation of 3,5-di-tert-butylcatechol to 3,5-di-tert-butyl-1,2-benzoquinone (catecholase activity) with dioxygen at ambient condition in good yields. The title complex shows dual effects, acts as an acid–base and also as a redox catalyst during the oxidation reaction.Figure optionsDownload full-size imageDownload high-quality image (56 K)Download as PowerPoint slide