Reorganization of unsaturated chemical bonds is one of the most promising strategies to generate architecturally diversified and innovative molecular library. Herein, we disclose a novel reorganization/cycloaddition between two imine units catalyzed by In(OTf)3 Lewis acid, which is sharply distinguished from the well-recognized [4+2] cycloaddition version with Povarov reaction. By means of this unprecedented imine chemistry, a collection of synthetically useful dihydroacridines have been synthesized with high functional group compatibility under concise reaction conditions. Preliminary mechanistic studies unravel that α,β-unsaturated imine likely serves as a pivotal intermediate. Notably, handing products give rise to a series of structurally novel and fine-tuneable acridinium photocatalysts, which offers a heuristic paradigm for synthesizing these ones and is also highlighted by facilitating several encouraging dihydrogen coupling reactions efficiently.
Herein, we disclose a novel reorganization/cycloaddition between two imine units catalyzed by In(OTf)3 Lewis acid, which is sharply distinguished from the well-recognized [4+2] cycloaddition version with Povarov reaction. By means...
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