Electrochemically Induced Ring-Opening/Friedel–Crafts Arylation of Chalcone Epoxides Catalyzed by a Triarylimidazole Redox Mediator

The indirect anodic oxidation of chalcone epoxides in the presence of electron-rich heteroarenes mediated by a triarylimidazole (Med) was investigated by cyclic voltammetry (CV) and controlled potential electrolysis. The CV results indicate that a homogeneous electron transfer between Med•+ and chal...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-01, Vol.80 (2), p.781-789
Main Authors: Lu, Nan-ning, Zhang, Ni-tao, Zeng, Cheng-Chu, Hu, Li-Ming, Yoo, Seung Joon, Little, R. Daniel
Format: Article
Language:English
Subjects:
Catalysis
Chalcones - chemistry
Epoxy Compounds
Imidazoles - chemistry
Molecular Structure
Oxidation-Reduction
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Summary:The indirect anodic oxidation of chalcone epoxides in the presence of electron-rich heteroarenes mediated by a triarylimidazole (Med) was investigated by cyclic voltammetry (CV) and controlled potential electrolysis. The CV results indicate that a homogeneous electron transfer between Med•+ and chalcone epoxides is facilitated by an electron-rich heteroarene that serves as an arylation reagent. The preparative scale electrolysis generated epoxide-ring-opened/Friedel–Crafts arylation products in moderate to good yields. The fact that only a catalytic amount of charge was required suggests that Med•+ initiates a chain reaction. In addition, overoxidation of the products is avoided even though their oxidation potential is less than that of the starting chalcone epoxides.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5022184