Interaction of 2-carbonyl and 2-hydroxy(or methoxy)alkyl benzimidazoles with arenes in the Brønsted superacid TfOH resulted in the formation of the corresponding Friedel-Crafts reaction products, 2-diarylmethyl and 2-arylmethyl substituted benzimidazoles in yields up to 90%. The reaction intermediates, N,O-diproptonated species derived from starting benzimidazoles in TfOH, were thorougly studied by means of NMR and DFT calculations. The plausible reaction mechanisms have been discussed.
Keywords: benzimidazoles; triflic acid; Friedel-Crafts reaction; cations
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Ryabukhin, D.; Turdakov, A.; Soldatova, N.; Kompanets, M.; Ivanov, A.; Boyarskaya, I.; Vasilyev, A. Beilstein Arch. 2019, 20196. doi:10.3762/bxiv.2019.6.v1
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