Superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups

A substrate has been prepared having two triarylmethanol centers and four pyridine-type substituent groups. Upon ionization in the Brønsted superacid CF(3)SO(3)H, the substrate undergoes two types of reactions. In the presence of only the superacid, the highly ionized intermediate(s) provide a doubl...

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Autores principales: Kennedy, Sean H, Gasonoo, Makafui, Klumpp, Douglas A
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/PMC6633208/
https://www.ncbi.nlm.nih.gov/pubmed/31354869
http://dx.doi.org/10.3762/bjoc.15.153
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author Kennedy, Sean H
Gasonoo, Makafui
Klumpp, Douglas A
author_facet Kennedy, Sean H
Gasonoo, Makafui
Klumpp, Douglas A
author_sort Kennedy, Sean H
collection PubMed
description A substrate has been prepared having two triarylmethanol centers and four pyridine-type substituent groups. Upon ionization in the Brønsted superacid CF(3)SO(3)H, the substrate undergoes two types of reactions. In the presence of only the superacid, the highly ionized intermediate(s) provide a double cyclization product having two pyrido[1,2-a]indole rings. With added benzene, an arylation product is obtained. A mechanism is proposed involving tetra-, penta-, or hexacationic species.
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spelling pubmed-66332082019-07-26 Superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups Kennedy, Sean H Gasonoo, Makafui Klumpp, Douglas A Beilstein J Org Chem Full Research Paper A substrate has been prepared having two triarylmethanol centers and four pyridine-type substituent groups. Upon ionization in the Brønsted superacid CF(3)SO(3)H, the substrate undergoes two types of reactions. In the presence of only the superacid, the highly ionized intermediate(s) provide a double cyclization product having two pyrido[1,2-a]indole rings. With added benzene, an arylation product is obtained. A mechanism is proposed involving tetra-, penta-, or hexacationic species. Beilstein-Institut 2019-07-09 /pmc/articles/PMC6633208/ /pubmed/31354869 http://dx.doi.org/10.3762/bjoc.15.153 Text en Copyright © 2019, Kennedy 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
Kennedy, Sean H
Gasonoo, Makafui
Klumpp, Douglas A
Superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups
title Superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups
title_full Superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups
title_fullStr Superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups
title_full_unstemmed Superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups
title_short Superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups
title_sort superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6633208/
https://www.ncbi.nlm.nih.gov/pubmed/31354869
http://dx.doi.org/10.3762/bjoc.15.153
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