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

ABSTRACT: 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.

SUBMITTER: Nan J 

PROVIDER: S-EPMC10189902 | biostudies-literature | 2023 May

REPOSITORIES: biostudies-literature

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

Nan Jiang J   Huang Guanjie G   Liu Shilei S   Wang Jing J   Ma Yangmin Y   Luan Xinjun X  

Chemical science 20230417 19

Herein, we disclose a novel reorganization/cycloaddition between two imine units catalyzed by In(OTf)<sub>3</sub> Lewis acid that differs from the well-known [4 + 2] cycloaddition version <i>via</i> 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 s  ...[more]

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