ArticleOrganometallics2015
In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides.
Article in Organometallics, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
11 citing papers in PubMed.
- Synthetic Strategies to Access Fluorinated Azoles.European journal of organic chemistry · 2025Article
- Cobalt(III) Halide Metal-Organic Frameworks Drive Catalytic Halogen Exchange.Journal of the American Chemical Society · 2024Article
- Electrochemical Synthesis of Unnatural Amino Acids Embedding 5- and 6-Membered Heteroaromatics.ACS omega · 2024Article
- Studying Regioisomer Formation in the Pd-Catalyzed Fluorination of Cyclic Vinyl Triflates: Evidence for in situ Ligand Modification.Angewandte Chemie (International ed. in English) · 2023Article
- Bismuth-Mediated α-Arylation of Acidic Diketones with ortho-Substituted Boronic Acids.Angewandte Chemie (International ed. in English) · 2022Article
- Different Oxidative Addition Mechanisms for 12- and 14-Electron Palladium(0) Explain Ligand-Controlled Divergent Site Selectivity.ACS catalysis · 2022Article
- Solvent coordination to palladium can invert the selectivity of oxidative addition.Chemical science · 2022Article
- HARC as an open-shell strategy to bypass oxidative addition in Ullmann-Goldberg couplings.Proceedings of the National Academy of Sciences of the United States of America · 2020Article
- Palladium-Catalyzed Fluorination of Cyclic Vinyl Triflates: Effect of TESCFAngewandte Chemie (International ed. in English) · 2016Article
- The Evolution of PdAccounts of chemical research · 2016Article
- Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.Chemical reviews · 2016Review
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is C-F reductive elimination of five-membered heteroaryl fluorides from Pd(II) complexes. On the basis of these studies, we have found that various heteroaryl bromides bearing phenyl groups in the ortho position can be effectively fluorinated under catalytic conditions. Highly activated 2-bromoazoles, such as 8-bromocaffeine, are also viable substrates for this reaction.
Identifiers
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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.