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The iron-catalyzed heterocyclizations from 2-nitroanilines and benzylic alcohols to form benzimidazoles using hydrogen transfer reaction were investigated in this study. In the presence of dppf in toluene at 150°C, various benzimidazoles were obtained in moderate to good yields within 24h. The reaction was proposed to proceed via a cascade of alcohol oxidation, nitro reduction, condensation, and dehydrogenation.
Pyridinium 1a underwent an efficient intramolecular cyclization initiated by fluoride ions to form highly fluorescent 1,3,4-triphenylpyrido[1,2-a]benzimidazole, providing a novel chemodosimeter for fluoride ions detection.
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