Reactions of 2-carbonyl and 2-hydroxy(or methoxy)alkyl substituted benzimidazoles with arenes in the superacid CF3SO3H. NMR and DFT study of dicationic electophilic species

Submitting author affiliation:
Saint Petersburg State Forest Technical University, Saint Petersburg, Russian Federation

Beilstein Arch. 2019, 20196. https://doi.org/10.3762/bxiv.2019.6.v1

Published 15 Apr 2019

Preprint

Abstract

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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