ArticleJournal of the American Chemical Society2015
Palladium-Catalyzed Arylation of Fluoroalkylamines.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed, 133 citations in OpenAlex.
- Unlocking Catalyst Activation as a Critical Bottleneck in Cross-Coupling Reactions: Room-Temperature Couplings of Weak Nucleophiles Enabled by [Pd(1-MeNAP)TFA]Angewandte Chemie (International ed. in English) · 2026Article
- The influence of the substituent type and position on the topology of 2-D heterometallic sodium-palladium(ii) coordination networks with substituted nicotinate ligands.RSC advances · 2026Article
- Kinetic Modeling Enables Understanding of Off-Cycle Processes in Pd-Catalyzed Amination of Five-Membered Heteroaryl Halides.Journal of the American Chemical Society · 2024Article
- Metallaphotocatalytic triple couplings for modular synthesis of elaborate N-trifluoroalkyl anilines.Nature communications · 2024Article
- The Versatile and StrategicChemical reviews · 2024Review
- The development of cage phosphine 'DalPhos' ligands to enable nickel-catalyzed cross-couplings of (hetero)aryl electrophiles.Chemical science · 2024Review
- "Sandwich" Diimine-Copper Catalyzed Trifluoroethylation and Pentafluoropropylation of Unactivated C(spChemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Reductive Arylation of Nitroarenes with Chloroarenes: Reducing Conditions Enable New Reactivity from Palladium Catalysts.Journal of the American Chemical Society · 2023Article
- Recent Advances ofMolecules (Basel, Switzerland) · 2023Review
- Important Role of NH-Carbazole in Aryl Amination Reactions Catalyzed by 2-Aminobiphenyl Palladacycles.ACS catalysis · 2023Article
- Iron porphyrin-catalyzedRSC advances · 2021Article
- Aryl Amination Using Soluble Weak Base Enabled by a Water-Assisted Mechanism.Journal of the American Chemical Society · 2020Article
- Development of an Aryl Amination Catalyst with Broad Scope Guided by Consideration of Catalyst Stability.Journal of the American Chemical Society · 2020Article
- Article
- An Improved PJournal of the American Chemical Society · 2020Article
- Nickel-Catalyzed Decarbonylative Amination of Carboxylic Acid Esters.Journal of the American Chemical Society · 2020Article
- Pd-Catalyzed C-N Coupling Reactions Facilitated by Organic Bases: Mechanistic Investigation Leads to Enhanced Reactivity in the Arylation of Weakly Binding Amines.ACS catalysis · 2019Article
- Breaking the Base Barrier: An Electron-Deficient Palladium Catalyst Enables the Use of a Common Soluble Base in C-N Coupling.Journal of the American Chemical Society · 2018Article
- Mechanistic Insight Leads to a Ligand Which Facilitates the Palladium-Catalyzed Formation of 2-(Hetero)Arylaminooxazoles and 4-(Hetero)Arylaminothiazoles.Angewandte Chemie (International ed. in English) · 2017Article
- A practical and catalyst-free trifluoroethylation reaction of amines using trifluoroacetic acid.Nature communications · 2017Article
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2 authors at 1 institution in 1 country.
Funding
Abstract
We report the synthesis of fluorinated anilines by palladium-catalyzed coupling of fluoroalkylamines with aryl bromides and aryl chlorides. The products of these reactions are valuable because anilines typically require the presence of an electron-withdrawing substituent on nitrogen to suppress aerobic or metabolic oxidation, and the fluoroalkyl groups have steric properties and polarity distinct from those of more common electron-withdrawing amide and sulfonamide units. The fluoroalkylaniline products are unstable under typical conditions for C-N coupling reactions (heat and strong base). However, the reactions conducted with the weaker base KOPh, which has rarely been used in cross-coupling to form C-N bonds, occurred in high yield in the presence of a catalyst derived from commercially available AdBippyPhos and [Pd(allyl)Cl]2. Under these conditions, the reactions occur with low catalyst loadings (<0.50 mol % for most substrates) and tolerate the presence of various functional groups that react with the strong bases that are typically used in Pd-catalyzed C-N cross-coupling reactions of aryl halides. The resting state of the catalyst is the phenoxide complex, (BippyPhosPd(Ar)OPh); due to the electron-withdrawing property of the fluoroalkyl substituent, the turnover-limiting step of the reaction is reductive elimination to form the C-N bond.
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