Reactions of 2-carbonyl- And 2-hydroxy(or methoxy)alkylsubstituted benzimidazoles with arenes in the superacid CF3SO3H. NMR and DFT studies of dicationic electrophilic species

Dmitry S. Ryabukhin, Alexey N. Turdakov, Natalia S. Soldatova, Mikhail O. Kompanets, Alexander Yu Ivanov, Irina A. Boyarskaya, Aleksander V. Vasilyev

Research output: Contribution to journalArticle

Abstract

Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkylbenzimidazoles 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, protonated species derived from starting benzimidazoles in TfOH, were thoroughly studied by means of NMR and DFT calculations and plausible reaction mechanisms are discussed.

Original languageEnglish
Pages (from-to)1962-1973
Number of pages12
JournalBeilstein Journal of Organic Chemistry
Volume15
DOIs
Publication statusPublished - 9 Aug 2019

Fingerprint

Benzimidazoles
Discrete Fourier transforms
Friedel-Crafts reaction
Nuclear magnetic resonance
Reaction intermediates
Reaction products

Keywords

  • Benzimidazoles
  • Cations
  • Friedel-Crafts reaction
  • Triflic acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Reactions of 2-carbonyl- And 2-hydroxy(or methoxy)alkylsubstituted benzimidazoles with arenes in the superacid CF3SO3H. NMR and DFT studies of dicationic electrophilic species. / Ryabukhin, Dmitry S.; Turdakov, Alexey N.; Soldatova, Natalia S.; Kompanets, Mikhail O.; Ivanov, Alexander Yu; Boyarskaya, Irina A.; Vasilyev, Aleksander V.

In: Beilstein Journal of Organic Chemistry, Vol. 15, 09.08.2019, p. 1962-1973.

Research output: Contribution to journalArticle

Ryabukhin, Dmitry S. ; Turdakov, Alexey N. ; Soldatova, Natalia S. ; Kompanets, Mikhail O. ; Ivanov, Alexander Yu ; Boyarskaya, Irina A. ; Vasilyev, Aleksander V. / Reactions of 2-carbonyl- And 2-hydroxy(or methoxy)alkylsubstituted benzimidazoles with arenes in the superacid CF3SO3H. NMR and DFT studies of dicationic electrophilic species. In: Beilstein Journal of Organic Chemistry. 2019 ; Vol. 15. pp. 1962-1973.
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