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

Marco Lessi; Gianmarco Panzetta; Giulia Marianetti; Fabio Bellina

doi:10.1055/s-0036-1589071

Synthesis, Table of Contents

Synthesis 2017; 49(20): 4676-4686
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

Marco Lessi

^aDipartimento di Chimica e Chimica Industriale, Università di Pisa, Via G. Moruzzi 13, 56124 Pisa, Italy Email: fabio.bellina@unipi.it

,

Gianmarco Panzetta

^aDipartimento di Chimica e Chimica Industriale, Università di Pisa, Via G. Moruzzi 13, 56124 Pisa, Italy Email: fabio.bellina@unipi.it

,

Giulia Marianetti

^bScuola Normale Superiore, Piazza dei Cavalieri 7, 56126 Pisa, Italy

,

Fabio Bellina *

^aDipartimento di Chimica e Chimica Industriale, Università di Pisa, Via G. Moruzzi 13, 56124 Pisa, Italy Email: fabio.bellina@unipi.it

› Author Affiliations

Abstract

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Dedicated to Prof. Renzo Rossi on the occasion of his 80^th 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 halides

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References

References

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