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Synthesis 2018; 50(02): 361-370
DOI: 10.1055/s-0036-1588585
DOI: 10.1055/s-0036-1588585
paper
Copper-Catalyzed Simultaneous Activation of C–H and N–H Bonds: Three-Component One-Pot Cascade Synthesis of Multisubstituted Imidazoles
Weitere Informationen
Publikationsverlauf
Received: 11. September 2017
Accepted after revision: 12. September 2017
Publikationsdatum:
10. Oktober 2017 (online)
§ Authors contributed equally to this work.
Abstract
A copper-catalyzed expedient, practical, and straightforward approach for the one-pot three-component modular synthesis of multisubstituted imidazoles has been described by using arylacetic acids, N-arylbenzamidines, and nitroalkanes. The reaction involves simultaneous activation of C–H and N–H bonds of arylacetic acids and N-arylbenzamidines, respectively. The use of inexpensive copper sulfate as a catalyst, readily available starting materials, and Celite-free workup makes this protocol economically viable. Multisubstituted imidazoles were obtained in moderate to good yields with significant functional group tolerance and high regioselectivity.
Key words
arylacetic acid - N-arylbenzamidine - C–H bond activation - N–H bond activation - CuSO4 - imidazoleSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1588585.
- Supporting Information
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