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volume 15 pages 1962-1973

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

Alexey N Turdakov 1
Mikhail O Kompanets 3
Irina A Boyarskaya 5
Publication typeJournal Article
Publication date2019-08-19
scimago Q2
wos Q3
SJR0.482
CiteScore3.8
Impact factor2.1
ISSN18605397
PubMed ID:  31501662
Organic Chemistry
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.

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Ryabukhin D. S. et al. 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 // Beilstein Journal of Organic Chemistry. 2019. Vol. 15. pp. 1962-1973.
GOST all authors (up to 50) Copy
Ryabukhin D. S., Turdakov A. N., Soldatova N., Kompanets M. O., Ivanov A. Yu., Boyarskaya I. A., Vasilyev A. 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 // Beilstein Journal of Organic Chemistry. 2019. Vol. 15. pp. 1962-1973.
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RIS Copy
TY - JOUR
DO - 10.3762/bjoc.15.191
UR - https://www.beilstein-journals.org/bjoc/articles/15/191
TI - 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
T2 - Beilstein Journal of Organic Chemistry
AU - Ryabukhin, Dmitry S.
AU - Turdakov, Alexey N
AU - Soldatova, Natalia
AU - Kompanets, Mikhail O
AU - Ivanov, Alexander Yu
AU - Boyarskaya, Irina A
AU - Vasilyev, Aleksander V
PY - 2019
DA - 2019/08/19
PB - Beilstein-Institut
SP - 1962-1973
VL - 15
PMID - 31501662
SN - 1860-5397
ER -
BibTex
Cite this
BibTex (up to 50 authors) Copy
@article{2019_Ryabukhin,
author = {Dmitry S. Ryabukhin and Alexey N Turdakov and Natalia Soldatova and Mikhail O Kompanets and Alexander Yu Ivanov and Irina A Boyarskaya and Aleksander V Vasilyev},
title = {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},
journal = {Beilstein Journal of Organic Chemistry},
year = {2019},
volume = {15},
publisher = {Beilstein-Institut},
month = {aug},
url = {https://www.beilstein-journals.org/bjoc/articles/15/191},
pages = {1962--1973},
doi = {10.3762/bjoc.15.191}
}