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Intermolecular versus Intramolecular Palladium-Catalyzed Direct Arylations between 1-(2-Bromobenzyl)imidazoles and Aryl Bromides

Abstract : Herein, we report on the sequential palladium-catalyzed intermol. followed by intramol. direct arylations of 1-(2-bromobenzyl)imidazoles. We found that, in the presence of 1 mol% palladium acetate and potassium acetate as base, the intermol. reaction between 1-(2-bromobenzyl)imidazole derivs. and electron-deficient aryl bromides proceeded faster than the intramol. reaction, allowing us to prep. medium-size polycyclic imidazoles after a second Pd-catalyzed intramol. arylation. These iterative direct arylations allowed the synthesis of fused nitrogen-contg. heterocycles with a 5- or 7-membered-ring in only two steps. Some reactions have also been performed as a one-pot procedure using 2 mol% of palladium acetate in the presence of a larger amt. of base (3 equiv.).
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01205447
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Submitted on : Friday, September 25, 2015 - 2:52:45 PM
Last modification on : Friday, July 10, 2020 - 4:00:49 PM

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Xiaowen Xu, Liqin Zhao, Yiqun Li, Jean-François Soulé, Henri Doucet. Intermolecular versus Intramolecular Palladium-Catalyzed Direct Arylations between 1-(2-Bromobenzyl)imidazoles and Aryl Bromides. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2015, 357 (13), pp.2869--2882. ⟨10.1002/adsc.201500332⟩. ⟨hal-01205447⟩

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