Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkyl-substituted benzimidazoles with arenes in the superacid CF(3)SO(3)H. NMR and DFT studies of dicationic electrophilic species

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 intermediate...

Descripción completa

Detalles Bibliográficos
Autores principales: Ryabukhin, Dmitry S, Turdakov, Alexey N, Soldatova, Natalia S, Kompanets, Mikhail O, Ivanov, Alexander Yu, Boyarskaya, Irina A, Vasilyev, Aleksander V
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6720581/
https://www.ncbi.nlm.nih.gov/pubmed/31501662
http://dx.doi.org/10.3762/bjoc.15.191
_version_ 1783448158995480576
author Ryabukhin, Dmitry S
Turdakov, Alexey N
Soldatova, Natalia S
Kompanets, Mikhail O
Ivanov, Alexander Yu
Boyarskaya, Irina A
Vasilyev, Aleksander V
author_facet Ryabukhin, Dmitry S
Turdakov, Alexey N
Soldatova, Natalia S
Kompanets, Mikhail O
Ivanov, Alexander Yu
Boyarskaya, Irina A
Vasilyev, Aleksander V
author_sort Ryabukhin, Dmitry S
collection PubMed
description 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.
format Online
Article
Text
id pubmed-6720581
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-67205812019-09-09 Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkyl-substituted benzimidazoles with arenes in the superacid CF(3)SO(3)H. 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 Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2019-08-19 /pmc/articles/PMC6720581/ /pubmed/31501662 http://dx.doi.org/10.3762/bjoc.15.191 Text en Copyright © 2019, Ryabukhin et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://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 Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
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)alkyl-substituted benzimidazoles with arenes in the superacid CF(3)SO(3)H. NMR and DFT studies of dicationic electrophilic species
title Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkyl-substituted benzimidazoles with arenes in the superacid CF(3)SO(3)H. NMR and DFT studies of dicationic electrophilic species
title_full Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkyl-substituted benzimidazoles with arenes in the superacid CF(3)SO(3)H. NMR and DFT studies of dicationic electrophilic species
title_fullStr Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkyl-substituted benzimidazoles with arenes in the superacid CF(3)SO(3)H. NMR and DFT studies of dicationic electrophilic species
title_full_unstemmed Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkyl-substituted benzimidazoles with arenes in the superacid CF(3)SO(3)H. NMR and DFT studies of dicationic electrophilic species
title_short Reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkyl-substituted benzimidazoles with arenes in the superacid CF(3)SO(3)H. NMR and DFT studies of dicationic electrophilic species
title_sort reactions of 2-carbonyl- and 2-hydroxy(or methoxy)alkyl-substituted benzimidazoles with arenes in the superacid cf(3)so(3)h. nmr and dft studies of dicationic electrophilic species
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6720581/
https://www.ncbi.nlm.nih.gov/pubmed/31501662
http://dx.doi.org/10.3762/bjoc.15.191
work_keys_str_mv AT ryabukhindmitrys reactionsof2carbonyland2hydroxyormethoxyalkylsubstitutedbenzimidazoleswitharenesinthesuperacidcf3so3hnmranddftstudiesofdicationicelectrophilicspecies
AT turdakovalexeyn reactionsof2carbonyland2hydroxyormethoxyalkylsubstitutedbenzimidazoleswitharenesinthesuperacidcf3so3hnmranddftstudiesofdicationicelectrophilicspecies
AT soldatovanatalias reactionsof2carbonyland2hydroxyormethoxyalkylsubstitutedbenzimidazoleswitharenesinthesuperacidcf3so3hnmranddftstudiesofdicationicelectrophilicspecies
AT kompanetsmikhailo reactionsof2carbonyland2hydroxyormethoxyalkylsubstitutedbenzimidazoleswitharenesinthesuperacidcf3so3hnmranddftstudiesofdicationicelectrophilicspecies
AT ivanovalexanderyu reactionsof2carbonyland2hydroxyormethoxyalkylsubstitutedbenzimidazoleswitharenesinthesuperacidcf3so3hnmranddftstudiesofdicationicelectrophilicspecies
AT boyarskayairinaa reactionsof2carbonyland2hydroxyormethoxyalkylsubstitutedbenzimidazoleswitharenesinthesuperacidcf3so3hnmranddftstudiesofdicationicelectrophilicspecies
AT vasilyevaleksanderv reactionsof2carbonyland2hydroxyormethoxyalkylsubstitutedbenzimidazoleswitharenesinthesuperacidcf3so3hnmranddftstudiesofdicationicelectrophilicspecies

Ejemplares similares