ArticleOrganic letters2015
Ligand-Controlled Regioselective Copper-Catalyzed Trifluoromethylation To Generate (Trifluoromethyl)allenes.
Article in Organic letters, 2015. 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.
- Electrochemical deoxygenative trifluoromethylallenylation of propargylic alcoholsChemical science · 2026Article
- Palladium-Catalyzed Decarbonylative Coupling of (Hetero)Aryl Boronate Esters with Difluorobenzyl Glutarimides.Organic letters · 2023Article
- Three-Component Approach to Densely Functionalized Trifluoromethyl Allenols by Asymmetric Organocatalysis.Journal of the American Chemical Society · 2023Article
- Decarbonylative Fluoroalkylation at Palladium(II): From Fundamental Organometallic Studies to Catalysis.Journal of the American Chemical Society · 2021Article
- Iron-Catalyzed Cross-Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols.Angewandte Chemie (International ed. in English) · 2021Article
- Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl Thioethers.ACS catalysis · 2020Article
- Catalytic One-Step Deoxytrifluoromethylation of Alcohols.The Journal of organic chemistry · 2019Article
- Article
- Enantioselective Formation of CFJournal of the American Chemical Society · 2017Article
- Metal-catalyzed Decarboxylative Fluoroalkylation Reactions.Synlett : accounts and rapid communications in synthetic organic chemistry · 2016Article
- Copper-Catalyzed Synthesis of Trifluoroethylarenes from Benzylic Bromodifluoroacetates.The Journal of organic chemistry · 2015Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
"Cu-CF3" species have been used historically for a broad spectrum of nucleophilic trifluoromethylation reactions. Although recent advancements have employed ligands to stabilize and harness the reactivity of this key organometallic intermediate, the ability of a ligand to differentiate a regiochemical outcome of a Cu-CF3-mediated or -catalyzed reaction has not been previously reported. Herein, we report the first example of a Cu-catalyzed trifluoromethylation reaction in which a ligand controls the regiochemical outcome. More specifically, we demonstrate the ability of bipyridyl-derived ligands to control the regioselectivity of the Cu-catalyzed nucleophilic trifluoromethylation reactions of propargyl electrophiles to generate (trifluoromethyl)allenes. This method provides a variety of di-, tri-, and tetrasubstituted (trifluoromethyl)allenes, which can be further modified to generate complex fluorinated substructures.
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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.