Synthesis of unsymmetrical 1,3-substituted-1,3-dihydro-benzimidazolones via copper-catalyzed C–N coupling under visible light

Although photoinduced copper catalysis for carbon–nitrogen (C–N) amine bond formation with alkyl/aryl halides has been developed, the potential of copper catalysis for the synthesis of 1,3-substituted benzimidazolone molecules remains mostly unexplored. We herein report for the first time that unsym...

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Bibliographic Details
Published in:New journal of chemistry 2022-07, Vol.46 (26), p.12465-12469
Main Authors: Liu, Jianjun, Zuo, Shengli, Huang, Jieying, Zhang, Fan, Zuo, Ang
Format: Article
Language:English
Subjects:
Bromides
Catalytic converters
Chemical synthesis
Copper
Coupling (molecular)
Halides
Nitrogen
Substitutes
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Summary:Although photoinduced copper catalysis for carbon–nitrogen (C–N) amine bond formation with alkyl/aryl halides has been developed, the potential of copper catalysis for the synthesis of 1,3-substituted benzimidazolone molecules remains mostly unexplored. We herein report for the first time that unsymmetrical 1,3-substituted-1,3-dihydro-benzimidazolones can be readily prepared from monosubstituted benzimidazolones with primary alkyl, allyl, and benzyl bromides in the presence of a catalytic amount of copper( i ) bromide and visible light. The catalytic system was optimized and a library of benzimidazolone products were converted in overall great yields up to 99%, demonstrating the utility of this approach for practical and green synthesis schemes.
ISSN:1144-0546
1369-9261
DOI:10.1039/D2NJ02054H