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Synthesis 2017; 49(20): 4676-4686
DOI: 10.1055/s-0036-1589071
DOI: 10.1055/s-0036-1589071
special topic
Improved Synthesis of Symmetrical 2,5-Diarylimidazoles by One-Pot Palladium-Catalyzed Direct Arylation Tailored on the Electronic Features of the Aryl Halide
This work was supported by the Università di Pisa under the projects PRA 2015 (project no. 2015_0038) and PRA 2017 (project no. 2017_28).Further Information
Publication History
Received: 22 May 2017
Accepted after revision: 19 June 2017
Publication Date:
31 July 2017 (online)
Dedicated to Prof. Renzo Rossi on the occasion of his 80th birthday
Published as part of the Special Topic Modern Strategies for Heterocycles Synthesis
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.
Key words
direct arylation - imidazoles - palladium - C–C coupling - regioselectivity - C–H bond activation - catalysis - aryl halidesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589071
- Supporting Information
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