ArticleNature chemistry2023
meta-Selective C-H arylation of phenols via regiodiversion of electrophilic aromatic substitution.
Article in Nature chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Programmable arene ring opening unlocks the diversification of phenols.Nature chemistry · 2026Article
- Total Synthesis of (±)-Integerrines B-F via Bismuth-Catalyzed Oxidative Homo- and Cross-Couplings of 3-Hydroxycarbazoles.Organic letters · 2026Article
- Ketone displacement and migration enabled by trifunctionalization of vinyl triflates.Nature communications · 2026Article
- Synthesis of 2-Arylphenols via Formal Bismuth(V)-Mediated C-O Arylation of Guaiacols.Organic letters · 2025Article
- Intermolecular Asymmetric Arylative Dearomatization of 1-Naphthols.Journal of the American Chemical Society · 2024Article
- Leveraging long-lived arenium ions in superacid for meta-selective methylation.Nature communications · 2024Article
- Transition Metal Mimetic π-Activation by Cationic Bismuth(III) Catalysts for Allylic C-H Functionalization of Olefins Using C═O and C═N Electrophiles.Journal of the American Chemical Society · 2024Article
- A para- to meta-isomerization of phenols.Nature chemistry · 2024Article
- CspChemical science · 2024Review
- Development and Scale-Up of a New Sulfone-Based Bismacycle as a Universal Precursor for Bi(V)-Mediated Electrophilic Arylation.Organic process research & development · 2024Article
- Organobismuth Compounds as Aryl Radical Precursors via Light-Driven Single-Electron Transfer.ACS catalysis · 2024Article
- sSPhos: A General Ligand for Enantioselective Arylative Phenol Dearomatization via Electrostatically-Directed Palladium Catalysis.Journal of the American Chemical Society · 2023Article
- Synthesis of Highly Functionalized Bismacycles via Post-Transmetallation Modification of Arylboronic Acids.The Journal of organic chemistry · 2023Article
- Recent Advances in Regioselective C-H Bond Functionalization of Free Phenols.Molecules (Basel, Switzerland) · 2023Review
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3 authors.
Funding
Abstract
Electrophilic aromatic substitution is among the most widely used mechanistic manifolds in organic chemistry. Access to certain substitution patterns is, however, precluded by intrinsic and immutable substituent effects that ultimately restrict the diversity of the benzenoid chemical space. Here we demonstrate that the established regioselectivity of electrophilic aromatic substitution can be overcome simply by diverting the key σ-complex intermediate towards otherwise inaccessible substitution products. This 'regiodiversion' strategy is realized through the development of a general and concise method for the meta-selective C-H arylation of sterically congested phenols. Consisting of a Bi(V)-mediated electrophilic arylation and a subsequent aryl migration/rearomatization, our process is orthogonal to conventional C-H activation and cross-coupling approaches, and does not require prefunctionalization of the substrate. Mechanistically informed applications in synthesis showcase its utility as a versatile and enabling route to highly functionalized, contiguously substituted aromatic building blocks that defy synthesis via existing methods.
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