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Facile access to fused 2D/3D rings via intermolecular cascade dearomative [2 + 2] cycloaddition/rearrangement reactions of quinolines with alkenes

Title	Facile access to fused 2D/3D rings via intermolecular cascade dearomative [2 + 2] cycloaddition/rearrangement reactions of quinolines with alkenes
Authors	Jiajia Ma, Shuming Chen, Peter Bellotti, Tobias Wagener, Constantin Daniliuc, Kendall N. Houk, Frank Glorius
Magazine	Nature Catalysis
Date	05/25/2022
DOI	10.1038/s41929-022-00784-5
Introduction	Fused two-dimensional/three-dimensional (2D/3D) rings are crucial pharmacophores in pharmaceutical agents, attributed to their distinct structural and physicochemical attributes. The preparation of these strained ring systems frequently necessitates intricate synthetic endeavours and often exhibits low efficiency, thereby presenting a significant limitation in pharmaceutical development. This study reports two types of energy-transfer-mediated cascade dearomative [2 + 2] cycloaddition/rearrangement reactions of quinoline derivatives with alkenes. These reactions provide a direct pathway to construct 2D/3D pyridine-fused 6-5-4-3- and 6-4-6-membered ring systems. Notably, this energy-transfer-mediated strategy demonstrates excellent diastereoselectivity, circumventing the general reactivity and selectivity issues associated with photochemical [2 + 2] cycloaddition of various other aromatics. Adjusting the aza-arene substitutions enabled selective redirection of the iridium photocatalysed energy transfer manifold towards either cyclopropanation or cyclobutane-rearrangement products. Density functional theory calculations confirm a cascade energy transfer mechanism is operative.
Quote	Jiajia Ma, Shuming Chen and Peter Bellotti et al. Facile access to fused 2D/3D rings via intermolecular cascade dearomative [2 + 2] cycloaddition/rearrangement reactions of quinolines with alkenes. Nat Catal. 2022. Vol. 5(5):405-413. DOI: 10.1038/s41929-022-00784-5
Element	Iridium (Ir)
Materials	Chemical Compounds
Industry	Pharmaceutical Industry

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