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Journal Article

Photocatalytic Oxidation of alpha-C-H Bonds in Unsaturated Hydrocarbons through a Radical Pathway Induced by a Molecular Cocatalyst

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Peng,  Baoxiang
Research Department Schlögl, Max Planck Institute for Chemical Energy Conversion, Max Planck Society;

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Muhler,  Martin
Research Department Schlögl, Max Planck Institute for Chemical Energy Conversion, Max Planck Society;

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Citation

Zhao, G., Hul, B., Busser, G. W., Peng, B., & Muhler, M. (2019). Photocatalytic Oxidation of alpha-C-H Bonds in Unsaturated Hydrocarbons through a Radical Pathway Induced by a Molecular Cocatalyst. ChemSusChem, 12(12), 2795-2801. doi:10.1002/cssc.201900394.


Cite as: https://hdl.handle.net/21.11116/0000-0006-79BE-D
Abstract
To improve the photocatalytic oxidation of alpha-C-H bonds in unsaturated hydrocarbons, N-hydroxyphthalimide (NHPI) was used as a molecular cocatalyst with CdS as the photoabsorber. Compared with previously reported photocatalysts involving solid cocatalysts, metal-free NHPI offers better sustainability in addition to the significantly enhanced performance as cocatalyst. The photogenerated holes were transferred into the more active phthalimide-N-oxyl radical (PINO) by reacting with NHPI. In this way, alpha-C-H bond oxidation was significantly improved through the activation by PINO; even for the sluggish toluene oxidation, the apparent quantum efficiency was as high as 36.5 %. The effects of substrates/NHPI concentration ratio, reaction temperature, and time as well as the reaction intermediates were comprehensively studied. It was possible to identify ketones/aldehydes as the primary products, and overoxidation was controlled by adjusting the substrates/NHPI concentration ratio and reaction time. Thus, the radical path induced by the NHPI-PINO redox pair is an efficient alternative to boost the sluggish photocatalytic oxidation of alpha-C-H bonds.