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

Abstract

Hybrid fused two-dimensional/three-dimensional (2D/3D) rings are important pharmacophores in drugs owing to their unique structural and physicochemical properties. Preparation of these strained ring systems often requires elaborate synthetic effort and exhibits low efficiency,thus representing a limiting factor in drug discovery. Here,we report two types of energy-transfer-mediated cascade dearomative [2 + 2] cycloaddition/rearrangement reactions of quinoline derivatives with alkenes, which provide a straightforward avenue to 2D/3D pyridine-fused 6-5-4-3- and 6-4-6-membered ring systems. Notably, this energy-transfer-mediated strategy features excellent diastereoselectivity that bypasses the general reactivity and selectivity issues of photochemical [2 + 2] cycloaddition of various other aromatics. Tuning the aza-arene substitutions enabled selective diversion of the iridium photocatalysed energy transfer manifold towards either cyclopropanation or cyclobutane-rearrangement products. Density functional theory calculations revealed a cascade energy transfer scenario to be operative.

Publisher

Nature Portfolio

Publication Date

5-1-2022

Publication Title

Nature Catalysis

Department

Chemistry and Biochemistry

Document Type

Article

DOI

https://dx.doi.org/10.1038/s41929-022-00784-5

Keywords

Photocycloaddition, Cycloaddition, Opportunities, Derivatives, Strategy, Arenes

Language

English

Format

text

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