In(OTf)(3)-catalyzed reorganization/cycloaddition of two imine units and subsequent modular assembly of acridinium photocatalysts

Herein, we disclose a novel reorganization/cycloaddition between two imine units catalyzed by In(OTf)(3) Lewis acid that differs from the well-known [4 + 2] cycloaddition version via the Povarov reaction. By means of this unprecedented imine chemistry, a collection of synthetically useful dihydroacr...

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Autores principales: Nan, Jiang, Huang, Guanjie, Liu, Shilei, Wang, Jing, Ma, Yangmin, Luan, Xinjun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10189902/
https://www.ncbi.nlm.nih.gov/pubmed/37206409
http://dx.doi.org/10.1039/d3sc00163f
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author Nan, Jiang
Huang, Guanjie
Liu, Shilei
Wang, Jing
Ma, Yangmin
Luan, Xinjun
author_facet Nan, Jiang
Huang, Guanjie
Liu, Shilei
Wang, Jing
Ma, Yangmin
Luan, Xinjun
author_sort Nan, Jiang
collection PubMed
description Herein, we disclose a novel reorganization/cycloaddition between two imine units catalyzed by In(OTf)(3) Lewis acid that differs from the well-known [4 + 2] cycloaddition version via the Povarov reaction. By means of this unprecedented imine chemistry, a collection of synthetically useful dihydroacridines has been synthesized. Notably, the obtained products give rise to a series of structurally novel and fine-tuneable acridinium photocatalysts, offering a heuristic paradigm for synthesis and efficiently facilitating several encouraging dihydrogen coupling reactions.
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spelling pubmed-101899022023-05-18 In(OTf)(3)-catalyzed reorganization/cycloaddition of two imine units and subsequent modular assembly of acridinium photocatalysts Nan, Jiang Huang, Guanjie Liu, Shilei Wang, Jing Ma, Yangmin Luan, Xinjun Chem Sci Chemistry Herein, we disclose a novel reorganization/cycloaddition between two imine units catalyzed by In(OTf)(3) Lewis acid that differs from the well-known [4 + 2] cycloaddition version via the Povarov reaction. By means of this unprecedented imine chemistry, a collection of synthetically useful dihydroacridines has been synthesized. Notably, the obtained products give rise to a series of structurally novel and fine-tuneable acridinium photocatalysts, offering a heuristic paradigm for synthesis and efficiently facilitating several encouraging dihydrogen coupling reactions. The Royal Society of Chemistry 2023-04-17 /pmc/articles/PMC10189902/ /pubmed/37206409 http://dx.doi.org/10.1039/d3sc00163f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Nan, Jiang
Huang, Guanjie
Liu, Shilei
Wang, Jing
Ma, Yangmin
Luan, Xinjun
In(OTf)(3)-catalyzed reorganization/cycloaddition of two imine units and subsequent modular assembly of acridinium photocatalysts
title In(OTf)(3)-catalyzed reorganization/cycloaddition of two imine units and subsequent modular assembly of acridinium photocatalysts
title_full In(OTf)(3)-catalyzed reorganization/cycloaddition of two imine units and subsequent modular assembly of acridinium photocatalysts
title_fullStr In(OTf)(3)-catalyzed reorganization/cycloaddition of two imine units and subsequent modular assembly of acridinium photocatalysts
title_full_unstemmed In(OTf)(3)-catalyzed reorganization/cycloaddition of two imine units and subsequent modular assembly of acridinium photocatalysts
title_short In(OTf)(3)-catalyzed reorganization/cycloaddition of two imine units and subsequent modular assembly of acridinium photocatalysts
title_sort in(otf)(3)-catalyzed reorganization/cycloaddition of two imine units and subsequent modular assembly of acridinium photocatalysts
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10189902/
https://www.ncbi.nlm.nih.gov/pubmed/37206409
http://dx.doi.org/10.1039/d3sc00163f
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