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

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Reactions of 2-carbonyl- And 2-hydroxy(or methoxy)alkylsubstituted benzimidazoles with arenes in the superacid CF<sub>3</sub>SO<sub>3</sub>H. NMR and DFT studies of dicationic electrophilic species'. Together they form a unique fingerprint.

  • Cite this