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  • Title: Photoredox-Enabled Dearomative [2π + 2σ] Cycloaddition of Phenols.
    Author: Dutta S, Lee D, Ozols K, Daniliuc CG, Shintani R, Glorius F.
    Journal: J Am Chem Soc; 2024 Jan 31; 146(4):2789-2797. PubMed ID: 38236061.
    Abstract:
    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 sp3-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.
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