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Published on: May 26, 2019
Copper-Catalyzed Electrochemical Selective Bromination of 8-Aminoquinoline Amide Using NH4Br as the Brominating
Xiang Yang1,2, Qi-Liang Yang2, Xiang-Yang Wang2
1Key Laboratory of Oil & Gas Fine Chemicals, Ministry of Education & Xinjiang Uyghur Autonomous Region, College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi, Xinjiang 830046, China.
Abstract:
A simple and mild protocol for copper-catalyzed bromination of quinoline at the C5 site of quinoline by anodic oxidation was developed, affording the desired remote C-H activation products with isolated yields of up to about 90%. The reaction proceeds with low-cost NH4Br and shows mild and green conditions (electricity as a green oxidant; NH3 and H2 as byproducts). At the same time, a gram-scale bromination reaction was also successfully fulfilled, showing its potential applicable value in organic synthesis. Moreover, the CV chart further demonstrated the proposed catalytic cycle.
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