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

Autor: Dmitry Ryabukhin, Alexey Turdakov, Natalia Soldatova, Mikhail Kompanets, Alexander Ivanov, Irina Boyarskaya, Aleksander Vasilyev
Rok vydání: 2019
DOI: 10.3762/bxiv.2019.6.v1
Popis: 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.
Databáze: OpenAIRE