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

  1. Dmitry Ryabukhin,
  2. Alexey Turdakov,
  3. Natalia Soldatova,
  4. Mikhail Kompanets,
  5. Alexander IvanovORCID Logo,
  6. Irina Boyarskaya and
  7. Aleksander VasilyevORCID Logo

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

Beilstein Arch. 2019, 20196.

Published 15 Apr 2019

  • Preprint


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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