A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins

A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones has been achieved by the coupling reactions of N-acyliminium ions produced from 3-hydroxyisoindol-1-ones or 5-hydroxy-1-pyrrol-2-ones with unactivated olefins in the presence of BF(3)·OEt(2) at room temperature. For...

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Detalles Bibliográficos
Autores principales: Lu, Nianhong, Wang, Lihong, Li, Zhanshan, Zhang, Wei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3302081/
https://www.ncbi.nlm.nih.gov/pubmed/22423287
http://dx.doi.org/10.3762/bjoc.8.21
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author Lu, Nianhong
Wang, Lihong
Li, Zhanshan
Zhang, Wei
author_facet Lu, Nianhong
Wang, Lihong
Li, Zhanshan
Zhang, Wei
author_sort Lu, Nianhong
collection PubMed
description A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones has been achieved by the coupling reactions of N-acyliminium ions produced from 3-hydroxyisoindol-1-ones or 5-hydroxy-1-pyrrol-2-ones with unactivated olefins in the presence of BF(3)·OEt(2) at room temperature. For most of the olefins, the reactions afforded the C(sp3)–C(sp2) cross-coupling products, but for the α-methylstyrene and 1-hexene, the C(sp3)–C(sp3) cross-coupling products were obtained.
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spelling pubmed-33020812012-03-15 A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins Lu, Nianhong Wang, Lihong Li, Zhanshan Zhang, Wei Beilstein J Org Chem Full Research Paper A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones has been achieved by the coupling reactions of N-acyliminium ions produced from 3-hydroxyisoindol-1-ones or 5-hydroxy-1-pyrrol-2-ones with unactivated olefins in the presence of BF(3)·OEt(2) at room temperature. For most of the olefins, the reactions afforded the C(sp3)–C(sp2) cross-coupling products, but for the α-methylstyrene and 1-hexene, the C(sp3)–C(sp3) cross-coupling products were obtained. Beilstein-Institut 2012-02-06 /pmc/articles/PMC3302081/ /pubmed/22423287 http://dx.doi.org/10.3762/bjoc.8.21 Text en Copyright © 2012, Lu et al. https://creativecommons.org/licenses/by/2.0https://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/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. 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
Lu, Nianhong
Wang, Lihong
Li, Zhanshan
Zhang, Wei
A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins
title A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins
title_full A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins
title_fullStr A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins
title_full_unstemmed A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins
title_short A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-acyliminium ions with unactivated olefins
title_sort concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of n-acyliminium ions with unactivated olefins
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3302081/
https://www.ncbi.nlm.nih.gov/pubmed/22423287
http://dx.doi.org/10.3762/bjoc.8.21
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