Article Dans Une Revue RSC Advances Année : 2022

Alkali halides as nucleophilic reagent sources for N-directed palladium-catalysed ortho -C–H halogenation of s -tetrazines and other heteroaromatics

Résumé

A general palladium-catalysed selective C-H halogenation reaction is reported, which was successfully achieved for a large variety of functionalized aromatic rings incorporating diverse N-directing groups. By using simple alkali halides of MX type as the nucleophilic reagent source (M = Li, Na, K, Cs and X = I, Br and Cl), and phenyliodanediacetate oxidant, clean C-H-iodination, bromination and chlorination reactions were performed. This general protocol of selective ortho-monohalogenation, which complements but contrasts with the classical methods using electrophilic reagents, is achievable in a short time (30 min) with microwave irradiation assistance. The reaction was extended to substrates bearing N-directing pyridine, pyrimidine, pyrazole, oxazoline, naphtho[1,2-d]thiazole, and azobenzene groups. Notably, the topical and selectivity-challenging s-tetrazine, as a nitrogen-rich heteroaromatic, was successfully halogenated by this protocol. This journal is © The Royal Society of Chemistry.

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hal-05028059 , version 1 (09-04-2025)

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Ahmad Daher, Oumaima Abidi, Jean-Cyrille Hierso, Julien Roger. Alkali halides as nucleophilic reagent sources for N-directed palladium-catalysed ortho -C–H halogenation of s -tetrazines and other heteroaromatics. RSC Advances, 2022, 12 (47), ⟨10.1039/d2ra06169d⟩. ⟨hal-05028059⟩
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