ArticleAngewandte Chemie (International ed. in English)2022
Bismuth-Mediated α-Arylation of Acidic Diketones with ortho-Substituted Boronic Acids.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 27 citations in OpenAlex.
- Article
- 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
- Enantioselective Synthesis of α-Arylated Allene Ketones Through Sequential Bismuth(V)-mediated Arylation and Organocatalytic Protonation.Angewandte Chemie (International ed. in English) · 2025Article
- Synthesis of 2-Arylphenols via Formal Bismuth(V)-Mediated C-O Arylation of Guaiacols.Organic letters · 2025Article
- Vinyltriarylbismuthonium Salts: Powerful Vehicles for α-Vinylation of Carbonyl Compounds.Journal of the American Chemical Society · 2024Article
- Organobismuth Compounds as Aryl Radical Precursors via Light-Driven Single-Electron Transfer.ACS catalysis · 2024Article
- 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
- Synthesis of Highly Functionalized Bismacycles via Post-Transmetallation Modification of Arylboronic Acids.The Journal of organic 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
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
Abstract
The α-arylation of cyclic and fluoroalkyl 1,3-diketones is made challenging by the highly stabilized nature of the corresponding enolates, and is especially difficult for sterically demanding aryl partners. As a general solution to this problem, we report the Bi-mediated oxidative coupling of acidic diones and ortho-substituted arylboronic acids. Starting from a bench-stable bismacycle precursor, a sequence of B-to-Bi transmetallation, oxidation and C-C bond formation furnishes the arylated diones. Development of methodology that tolerates both sensitive functionality and steric demand is supported by interrogation of key reactive intermediates. Application of our strategy to cyclic diones enables the concise synthesis of important agrochemical intermediates which were previously prepared using toxic Pb reagents. This methodology also enables the first ever arylation of fluoroalkyl diones which, upon condensation with hydrazine, provides direct access to valuable fluoroalkyl pyrazoles.
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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.