Improved Synthesis of Symmetrical 2,5-Diarylimidazoles by One-Pot Palladium-Catalyzed Direct Arylation Tailored on the Electronic Features of the Aryl Halide.

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Title: Improved Synthesis of Symmetrical 2,5-Diarylimidazoles by One-Pot Palladium-Catalyzed Direct Arylation Tailored on the Electronic Features of the Aryl Halide.
Authors: Lessi, Marco1, Panzetta, Gianmarco1, Marianetti, Giulia2, Bellina, Fabio1 fabio.bellina@unipi.it
Source: Synthesis. 2017, Vol. 49 Issue 20, p4676-4686. 11p.
Subjects: Imidazoles, Chemical synthesis, Palladium catalysts, Arylation, Electronic structure, Aryl halides
Abstract: Two methods for the one-pot synthesis of 2,5-diarylimidazoles by palladium-catalyzed direct C--H arylation of 1-substituted imidazoles with aryl bromides have been devised. The first method, promoted by copper(I) iodide, is best suited for electron-poor aryl bromides, and also allows the 2,5-diarylation of thiazole and oxazole. The use of xylene instead of DMA is the key for the efficiency of the second method, which gives the best results with electron-rich aryl bromides. [ABSTRACT FROM AUTHOR]
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Database: Engineering Source
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Abstract:Two methods for the one-pot synthesis of 2,5-diarylimidazoles by palladium-catalyzed direct C--H arylation of 1-substituted imidazoles with aryl bromides have been devised. The first method, promoted by copper(I) iodide, is best suited for electron-poor aryl bromides, and also allows the 2,5-diarylation of thiazole and oxazole. The use of xylene instead of DMA is the key for the efficiency of the second method, which gives the best results with electron-rich aryl bromides. [ABSTRACT FROM AUTHOR]
ISSN:00397881
DOI:10.1055/s-0036-1589071