Reactivity of 4-phenylthiazoles in ruthenium catalyzed direct arylations

Abstract : The reactivity of the phenyl substituent of 4-phenylthiazoles in Ru-catalyzed direct arylation was studied. 4-Phenylthiazole was found to be unreactive; whereas, the introduction of an aryl unit at C5-position of 4-phenylthiazole enhances its reactivity, allowing the selective mono-arylation of the phenyl unit of 4-phenylthiazoles in moderate to high yields using 5 mol% of [Ru(p-cymene)Cl 2 ] 2 catalyst precursor associated to KOPiv as base. These results reveal that the conformation and electronic properties of 4-phenylthiazoles are crucial to allow the formation of suitable intermediates in the course of the catalytic cycle. The reaction tolerated both electron-rich and electron-poor aryl bromides allowing the straightforward tuning of the electronic properties of the arylated 2-methyl-4-phenyl-5-arylthiazoles. © 2019 John Wiley and Sons, Ltd.
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A. Daher, D. Jacquemin, V. Guerchais, Jean-François Soulé, H. Doucet. Reactivity of 4-phenylthiazoles in ruthenium catalyzed direct arylations. Applied Organometallic Chemistry, Wiley-Blackwell, 2019, 33 (4), pp.e4794. ⟨10.1002/aoc.4794⟩. ⟨hal-02090015⟩



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