ArticleNature chemistry2020
Modular bismacycles for the selective C-H arylation of phenols and naphthols.
Article in Nature chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.
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Who cites it
27 citing papers in PubMed, 95 citations in OpenAlex.
- Regiospecific α-arylation of diverse carbonyl compounds using an organobismuth transporter.Nature chemistry · 2026Article
- On the Ability of Bismuth to Couple Weakly Coordinating Anions.Angewandte Chemie (International ed. in English) · 2026Article
- Total Synthesis of (±)-Integerrines B-F via Bismuth-Catalyzed Oxidative Homo- and Cross-Couplings of 3-Hydroxycarbazoles.Organic letters · 2026Article
- From Boron to Bismuth: The Pre-transmetalation Complex in the Aryl Transfer.Journal of the American Chemical Society · 2026Article
- Steric Pruning Unlocks Hierarchical Structuring, Thermochromism, C-H/O Activation, and 6-electron Redox Transmetalation in Planar Bismuth Triamides.Angewandte Chemie (International ed. in English) · 2026Article
- Enantioselective Synthesis of α-Arylated Allene Ketones Through Sequential Bismuth(V)-mediated Arylation and Organocatalytic Protonation.Angewandte Chemie (International ed. in English) · 2025Article
- Ligand-Controlled Chemodivergent Bismuth Catalysis.Journal of the American Chemical Society · 2025Article
- Synthesis of 2-Arylphenols via Formal Bismuth(V)-Mediated C-O Arylation of Guaiacols.Organic letters · 2025Article
- Red-Light-ActiveJournal of the American Chemical Society · 2025Article
- 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
- Oxidative Addition of Aryl Electrophiles into a Red-Light-Active Bismuthinidene.Journal of the American Chemical Society · 2023Article
- Electrochemical synthesis of biaryls by reductive extrusion from N,N'-diarylureas.Nature communications · 2023Article
- Synthesis of Highly Functionalized Bismacycles via Post-Transmetallation Modification of Arylboronic Acids.The Journal of organic chemistry · 2023Article
- Synthesis, Isolation, and Characterization of Two Cationic Organobismuth(II) Pincer Complexes Relevant in Radical Redox Chemistry.Journal of the American Chemical Society · 2023Article
- meta-Selective C-H arylation of phenols via regiodiversion of electrophilic aromatic substitution.Nature chemistry · 2023Article
- Umpolung Synthesis of Pyridyl Ethers by BiAngewandte Chemie (International ed. in English) · 2022Article
- Bismuth-Mediated α-Arylation of Acidic Diketones with ortho-Substituted Boronic Acids.Angewandte Chemie (International ed. in English) · 2022Article
- Mechanism of the Aryl-F Bond-Forming Step from Bi(V) Fluorides.Journal of the American Chemical Society · 2022Article
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Authors and funding
4 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Given the important role played by 2-hydroxybiaryls in organic, medicinal and materials chemistry, concise methods for the synthesis of this common motif are extremely valuable. In seeking to extend the lexicon of synthetic chemists in this regard, we have developed an expedient and general strategy for the ortho-arylation of phenols and naphthols using readily available boronic acids. Our methodology relies on in situ generation of a uniquely reactive Bi(V) arylating agent from a bench-stable Bi(III) precursor via telescoped B-to-Bi transmetallation and oxidation. By exploiting reactivity that is orthogonal to conventional metal-catalysed manifolds, diverse aryl and heteroaryl partners can be rapidly coupled to phenols and naphthols under mild conditions. Following arylation, high-yielding recovery of the Bi(III) precursor allows for its efficient re-use in subsequent reactions. Mechanistic interrogation of each key step of the methodology informs its practical application and provides fundamental insight into the underexploited reactivity of organobismuth compounds.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.