Photoelectrocatalytic C–H halogenation over an oxygen vacancy-rich TiO2 photoanode

Zhenhua Li, Lan Luo, Min Li, Wangsong Chen, Yuguang Liu, Jiangrong Yang, Si-Min Xu, Hua Zhou, Lina Ma, Ming Xu, Xianggui Kong and Haohong Duan ()
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Zhenhua Li: Beijing University of Chemical Technology
Lan Luo: Beijing University of Chemical Technology
Min Li: Tsinghua University
Wangsong Chen: Beijing University of Chemical Technology
Yuguang Liu: Beijing University of Chemical Technology
Jiangrong Yang: Beijing University of Chemical Technology
Si-Min Xu: Beijing University of Chemical Technology
Hua Zhou: Tsinghua University
Lina Ma: Beijing University of Chemical Technology
Ming Xu: Beijing University of Chemical Technology
Xianggui Kong: Beijing University of Chemical Technology
Haohong Duan: Tsinghua University

Nature Communications, 2021, vol. 12, issue 1, 1-13

Abstract: Abstract Photoelectrochemical cells are emerging as powerful tools for organic synthesis. However, they have rarely been explored for C–H halogenation to produce organic halides of industrial and medicinal importance. Here we report a photoelectrocatalytic strategy for C–H halogenation using an oxygen-vacancy-rich TiO2 photoanode with NaX (X=Cl−, Br−, I−). Under illumination, the photogenerated holes in TiO2 oxidize the halide ions to corresponding radicals or X2, which then react with the substrates to yield organic halides. The PEC C–H halogenation strategy exhibits broad substrate scope, including arenes, heteroarenes, nonpolar cycloalkanes, and aliphatic hydrocarbons. Experimental and theoretical data reveal that the oxygen vacancy on TiO2 facilitates the photo-induced carriers separation efficiency and more importantly, promotes halide ions adsorption with intermediary strength and hence increases the activity. Moreover, we designed a self-powered PEC system and directly utilised seawater as both the electrolyte and chloride ions source, attaining chlorocyclohexane productivity of 412 µmol h−1 coupled with H2 productivity of 9.2 mL h−1, thus achieving a promising way to use solar for upcycling halogen in ocean resource into valuable organic halides.

Date: 2021
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DOI: 10.1038/s41467-021-26997-z

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