Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

Generation and Confinement of Long-Lived N-Oxyl Radical and Its Photocatalysis

Generation and Confinement of Long-Lived N-Oxyl Radical and Its Photocatalysis
Zhipeng Huang, Chaofeng Zhang, Jianmin Lu, Nengchao Luo, Feng Wang
Generation of controllable carbon radical under the assistance of N-oxyl radical is an efficient method for the activation of C–H bonds in hydrocarbons. We herein report that irradiation of α-Fe2O3 and N-hydroxyphthalimide (NHPI) under 455 nm light generates phthalimide-N-oxyl radical (PINO*), which after being formed by oxidation with holes, is confined on α-Fe2O3 surface. The half-life time of the confined radical reaches 22 s as measured by in situ electron paramagnetic resonance (EPR) after the light being turned off. This allows the long-lived N-oxyl radical to abstract the H from C–H bond to form a carbon radical that reacts with molecular oxygen to form R3C–OO· species, decomposition of which leads to oxygenated products.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b12928

DOI: 10.1021/jacs.7b12928

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