Abstract

Photocatalysis driven under visible light allows us to carry out hydrocarbon oxofunctionalization under ambient conditions, using molecular oxygen as a sacrificial reagent, with the absence of hazardous subproducts and the potential use of the Sun as a clean and low-cost source of light. In this work, eight materials-five based on titanium dioxide and three based on bismuth oxyhalides-were used as photocatalysts in the selective oxofunctionalization of cyclohexene. The cyclohexane oxofunctionalization reactions were performed inside of a homemade photoreactor equipped with a 400 W metal halide lamp and injected air as a source of molecular oxygen. In all assayed systems, the main oxygenated products, identified by mass spectrometry, were 1,2-epoxycyclohexane, 2-cyclohexen-1-ol, and 2-cyclohexen-1-one. Titanium dioxide-based materials exhibited higher selectivities for 1,2-epoxycyclohexane than bismuth oxyhalide-based materials. In addition to this, titanium dioxide doped with iron exhibited the best selectivity for 1,2-epoxycyclohexane, demonstrating that iron plays a relevant role in the cyclohexene epoxidation process.