Regioselective Monoarylation of 2-Phenylbenzimidazole via Ruthenium-Catalyzed­ C–H Bond Functionalization

Abstract The highly regioselective monoarylation of 1-methyl-2-phenyl-1 H -benzimidazole has been demonstrated. The reaction of 1-methyl-2-phenyl-1 H -benzimidazole with 4-iodoanisole provided 2-(4′-methoxybiphenyl-2-yl)-1-methyl-1 H -benzimidazole as the sole product in 96% isolated yield in the pr...

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Veröffentlicht in:Synthesis (Stuttgart) 2014-08, Vol.46 (23), p.3185-3190
Hauptverfasser: Kobayashi, Yasuyuki, Kashiwa, Mitsuhiro, Sonoda, Motohiro, Kirihata, Mitsunori, Tanimori, Shinji
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract The highly regioselective monoarylation of 1-methyl-2-phenyl-1 H -benzimidazole has been demonstrated. The reaction of 1-methyl-2-phenyl-1 H -benzimidazole with 4-iodoanisole provided 2-(4′-methoxybiphenyl-2-yl)-1-methyl-1 H -benzimidazole as the sole product in 96% isolated yield in the presence of [RuCl 2 ( p -cymene)] 2 and triphenylphosphine as precatalysts. A series of novel 2-(biphenyl-2-yl)benzimidazoles have been synthesized in good to excellent yields.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0034-1379013