Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 2, Pages 781-789Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo5022184
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Funding
- National Natural Science Foundation of China [21272021, 21472011]
- National Key Technology RD Program [2011BAD23B01]
- Beijing City Education Committee [KM201010005009]
- US National Science Foundation [OISE-0968399]
- Office Of The Director
- Office Of Internatl Science &Engineering [0968399] Funding Source: National Science Foundation
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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(center dot+) 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(center dot+) 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.
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