Photoredox-Enabled Dearomative [2π + 2σ] Cycloaddition of Phenols

Dearomative photocycloaddition of monocyclic arenes is an appealing strategy for comprehending the concept of “escape from flatland”. This brings the replacement of readily available planar aromatic hydrocarbon units with a 3D fused bicyclic core with sp 3-enriched carbon units. Herein, we outline a...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2024-01, Vol.146 (4), p.2789-2797
Main Authors: Dutta, Subhabrata, Lee, Donghyeon, Ozols, Kristers, Daniliuc, Constantin G., Shintani, Ryo, Glorius, Frank
Format: Article
Language:English
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Summary:Dearomative photocycloaddition of monocyclic arenes is an appealing strategy for comprehending the concept of “escape from flatland”. This brings the replacement of readily available planar aromatic hydrocarbon units with a 3D fused bicyclic core with sp 3-enriched carbon units. Herein, we outline an intermolecular approach for the dearomative photocycloaddition of phenols. In order to circumvent the ground-state aromaticity and to construct conformationally restrained building blocks, bicyclo[1.1.0]­butanes were chosen as coupling partners. This dearomative approach renders straightforward access to a bicyclo[2.1.1]­hexane unit fused to a cyclic enone moiety, which further contributed as a synthetic linchpin for postmodifications. Mechanistic experiment advocates for a plausible onset from both the reactants, depending on the redox potential.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.3c12894