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Chlorine Radical‐Mediated Photocatalytic C─C Coupling of Methanol to Ethylene Glycol with Near‐Unity Selectivity

Guang‐Xing Dong, Meng‐Ran Zhang, Meng‐Ran Zhang, Su‐Xian Yuan, Min Zhang, Min Zhang, Tong‐Bu Lu

2025Angewandte Chemie International Edition13 citationsDOI

Abstract

Abstract The selective activation of inert C─H bonds in methanol under mild conditions to synthesize high‐value C 2 products remains a formidable challenge, primarily due to the competing high reactivity of O─H bonds. Herein, we pioneer a chlorine radical‐mediated strategy to redirect the photocatalytic reaction pathway for methanol conversion toward ethylene glycol (EG). Efficient C─H bond activation is achieved by constructing a Z‐scheme heterojunction photocatalyst (ZnIn 2 S 4 /TiO 2 ‐Cl) composed of chlorinated TiO 2 (TiO 2 ‐Cl) and ZnIn 2 S 4 with efficient charge separation. Photogenerated holes in this system preferentially oxidize surface‐adsorbed Cl − to chlorine radicals (Cl•). These radicals drive a thermodynamically favorable hydrogen atom transfer via hydrogen abstraction, cleaving the C─H bond of methanol to form hydroxymethyl radicals (•CH 2 OH). Subsequent C─C coupling of •CH 2 OH intermediates, synergistically combined with a self‐sustaining Cl − /Cl• cycle, produces EG with exceptional selectivity (96.7%) and yield (21.6 mmol g −1 ) while suppressing overoxidation. In contrast, nonchlorinated catalysts predominantly utilize photogenerated holes for O─H bond cleavage under identical conditions, yielding only C 1 products (HCHO, HCOOH). This work not only establishes a solar‐driven approach for methanol valorization but also advances mechanistic insights into radical‐mediated pathway control in heterogeneous photocatalysis.

Topics & Concepts

SelectivityEthylene glycolMethanolChemistryPhotochemistryEthyleneChlorinePhotocatalysisCoupling (piping)Materials scienceOrganic chemistryCatalysisMetallurgyFluorine in Organic ChemistryRadical Photochemical ReactionsCO2 Reduction Techniques and Catalysts
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