Visible light-induced FeCl3-catalyzed chlorination of C–H bonds with MgCl2

Chlorination has become a commonly used strategy in various chemical industries. Environmentally friendly chlorination of C–H bonds to directly generate C–Cl bonds is also in high demand in organic synthesis. Herein, we report a new and green highly selective method of chlorination of C(sp3)–H moiet...

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Published in:Green chemistry : an international journal and green chemistry resource : GC 2024, Vol.26 (11), p.6559-6569
Main Authors: Huang, Jing, Liu, Yidong, Tian, Xia, Shao-Fei Ni, Shen, Li, Zhan-Hui, Zhang, Li, Dong, Liu, Shouxin
Format: Article
Language:English
Subjects:
Chlorination
Electron spin
Ferric chloride
Free radicals
Inorganic salts
Light effects
Magnesium chloride
Oxidants
Oxidizing agents
Reaction mechanisms
Selectivity
Spin resonance
Toluene
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Summary:Chlorination has become a commonly used strategy in various chemical industries. Environmentally friendly chlorination of C–H bonds to directly generate C–Cl bonds is also in high demand in organic synthesis. Herein, we report a new and green highly selective method of chlorination of C(sp3)–H moieties with the inorganic salt MgCl2, cocatalyzed by visible light/FeCl3 under strong oxidant-free and ambient conditions. The reaction was applied to the chlorination of different methylarene α-hydrogen and cyclic hydrocarbon C–H moieties with high conversion and kinetic selectivity. The chlorination of toluene α-Hs proceeded in 91% yield, with 98% selectivity and 95% conversion. Electron–spin resonance studies of the DMPO-Cl (5,5-dimethyl-1-pyrroline-N-oxide) radical revealed that the reaction mechanism involved a free radical process.
ISSN:1463-9262
1463-9270
DOI:10.1039/d4gc00664j