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

Dmitry Ryabukhin; Alexey Turdakov; Natalia Soldatova; Mikhail Kompanets; Alexander Ivanov; Irina Boyarskaya; Aleksander Vasilyev

doi:10.3762/bxiv.2019.6.v1

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

Dmitry Ryabukhin ,
Alexey Turdakov ,
Natalia Soldatova ,
Mikhail Kompanets ,
Alexander Ivanov ,
Irina Boyarskaya and
Aleksander Vasilyev

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

PDF

Read the peer-reviewed version of this preprint: https://doi.org/10.3762/bjoc.15.191

SUBJECT AREAS

Show All Preprints Nanotechnology Organic chemistry Bioorganic chemistry / chemical biology Catalysis Chemical methods and reactions Flow and process chemistry Green and sustainable chemistry Materials chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry

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

Supporting Information

Format: DOC

Size: 8.1 MB

Download

How to Cite

When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

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

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

File format:

RIS

BibTeX

Download

© 2019 Ryabukhin et al.; licensee Beilstein-Institut.
This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited.
The license is subject to the Beilstein Archives terms and conditions: (https://www.beilstein-archives.org/xiv/terms)

aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)