ArticleJournal of the American Chemical Society2019
Palladium-Catalyzed α-Arylation of Carboxylic Acids and Secondary Amides via a Traceless Protecting Strategy.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Synthesis, structural characterization, and dual DNA/HSA binding of novel Palladium(II) violurate complex with selective p53/Caspase-3-mediated anticancer activity.Scientific reports · 2026Article
- Photocatalyst-Dependent Enantioselectivity in the Light-Driven Deracemization of Cyclic α-Aryl Ketones.Journal of the American Chemical Society · 2025Article
- Applications of Transition Metal-CatalyzedChemical reviews · 2024Review
- Diastereo- and Enantioselective Reductive Mannich-type Reaction of α,β-Unsaturated Carboxylic Acids to Ketimines: A Direct Entry to Unprotected βChemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Exploiting Coordination Effects for the Regioselective Zincation of Diazines Using TMPZnX⋅LiX (X=Cl, Br).Angewandte Chemie (International ed. in English) · 2022Article
- An Expedient Method for the Umpolung Coupling of Enols with Heteronucleophiles.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Modular synthesis of α-arylated carboxylic acids, esters and amidesChemical science · 2022Article
- Palladium-catalyzed chemoselective direct α-arylation of carbonyl compounds with chloroaryl triflates at the C-Cl site.Chemical science · 2022Article
- Recent Advances in the Synthesis of Ibuprofen and Naproxen.Molecules (Basel, Switzerland) · 2021Review
- Coupling of Reformatsky Reagents with Aryl Chlorides Enabled by Ylide-Functionalized Phosphine Ligands.Angewandte Chemie (International ed. in English) · 2021Article
- Computational Analysis of Enantioselective Pd-Catalyzed α-Arylation of Ketones.The Journal of organic chemistry · 2020Article
- A direct route to six and seven membered lactonesChemical science · 2020Article
- Deoxygenative α-alkylation and α-arylation of 1,2-dicarbonyls.Chemical science · 2020Article
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Authors and funding
2 authors.
Funding
Abstract
A novel traceless protecting strategy is presented for the long-standing challenge of conducting the palladium-catalyzed α-arylation of carboxylic aids and secondary amides with aryl halides. Both of the presented coupling processes occur with a variety of carboxylic acids and amides and with a variety of aryl bromides containing a broad range of functional groups, including base-sensitive functionality like acyl, alkoxycarbonyl, nitro, cyano, and even hydroxyl groups. Five commercial drugs were prepared through this method in one step in 81-96% yield. Gram-scale synthesis of medication Naproxen and Flurbiprofen with low palladium loading further highlights the practical value of this method.
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