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 CF3SO3H, the substrate undergoes two types of reactions. In the presence of only the superacid, the highly ionized intermediate(s) provide a double cy...

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Main Authors:	Sean H. Kennedy, Makafui Gasonoo, Douglas A. Klumpp
Format:	Article
Language:	English
Published:	Beilstein-Institut 2019-07-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	cation Friedel–Crafts heterocycle superacid superelectrophile
Online Access:	https://doi.org/10.3762/bjoc.15.153

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spelling	doaj-1c4c154f0a1949aa913cb34acc66d12b2021-04-02T12:02:37ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972019-07-011511515152010.3762/bjoc.15.1531860-5397-15-153Superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groupsSean H. Kennedy0Makafui Gasonoo1Douglas A. Klumpp2Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60178, USADepartment of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60178, USADepartment of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60178, USAA substrate has been prepared having two triarylmethanol centers and four pyridine-type substituent groups. Upon ionization in the Brønsted superacid CF3SO3H, 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.https://doi.org/10.3762/bjoc.15.153cationFriedel–Craftsheterocyclesuperacidsuperelectrophile
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Sean H. Kennedy Makafui Gasonoo Douglas A. Klumpp
spellingShingle	Sean H. Kennedy Makafui Gasonoo Douglas A. Klumpp Superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups Beilstein Journal of Organic Chemistry cation Friedel–Crafts heterocycle superacid superelectrophile
author_facet	Sean H. Kennedy Makafui Gasonoo Douglas A. Klumpp
author_sort	Sean H. Kennedy
title	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_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_sort	superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2019-07-01
description	A substrate has been prepared having two triarylmethanol centers and four pyridine-type substituent groups. Upon ionization in the Brønsted superacid CF3SO3H, 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.
topic	cation Friedel–Crafts heterocycle superacid superelectrophile
url	https://doi.org/10.3762/bjoc.15.153
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Superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups

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