ArticleAngewandte Chemie (International ed. in English)2020
Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 37 papers.
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Who cites it
37 citing papers in PubMed.
- Quaternary Carbons from Amines and Acids.Journal of the American Chemical Society · 2026Article
- Radical/Ylide-Tunable Pyridinium Salt Enables Photo/Thermocatalytic Divergent [3 + 2] Cycloadditions.JACS Au · 2026Article
- Article
- Ni-Catalyzed Electrochemical Carbonylative Ketone Synthesis Employing a Radical Sorting Strategy.Angewandte Chemie (International ed. in English) · 2026Article
- Cobalt-catalyzed reductive cross-coupling: a review.Molecular diversity · 2025Review
- Article
- A comprehensive review on carbonylation reactions: catalysis by magnetic nanoparticle-supported transition metals.Nanoscale advances · 2025Review
- Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis.Chemical reviews · 2024Review
- Reductive deaminative cross-coupling of alkyl bistriflimides enabled by electrocatalysis.Science advances · 2024Article
- Ni-Catalyzed Electro-Reductive Cross-Electrophile Couplings of Alkyl Amine-Derived Radical Precursors with Aryl Iodides.The Journal of organic chemistry · 2024Article
- A decarbonylative approach to alkylnickel intermediates and C(spScience (New York, N.Y.) · 2024Article
- Synthesis of Secondary Boronates via Deaminative Cross-Coupling of Alkyl Nitroso Carbamates and Boronic Acids.Angewandte Chemie (International ed. in English) · 2024Article
- Synthesis of Stereodefined Enones from the Cross-Electrophile Coupling of Activated Acrylic Acids with Alkyl Bromides.Organic letters · 2024Article
- Chloroimidazolium Deoxyfluorination Reagent with HThe Journal of organic chemistry · 2024Article
- Ligand Relay for Nickel-Catalyzed Decarbonylative Alkylation of Aroyl Chlorides.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Synthesis of Phenol-Pyridinium Salts Enabled by Tandem Electron Donor-Acceptor Complexation and Iridium Photocatalysis.The Journal of organic chemistry · 2024Article
- Nickel-Catalyzed Enantioselective Decarboxylative Acylation: Rapid, Modular Access to α-Amino Ketones.Angewandte Chemie (International ed. in English) · 2023Article
- Synthetic Advantages of Defluorinative C-F Bond Functionalization.Angewandte Chemie (International ed. in English) · 2023Review
- Oxidative Cross Dehydrogenative Coupling ofJournal of the American Chemical Society · 2023Article
- Harnessing Sulfur(VI) Fluoride Exchange Click Chemistry and Photocatalysis for Deaminative Benzylic Arylation.ACS catalysis · 2023Article
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4 authors.
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Abstract
While ketones are among the most versatile functional groups, their synthesis remains reliant upon reactive and low-abundance starting materials. In contrast, amide formation is the most-used bond-construction method in medicinal chemistry because the chemistry is reliable and draws upon large and diverse substrate pools. A new method for the synthesis of ketones is presented here that draws from the same substrates used for amide bond synthesis: amines and carboxylic acids. A nickel terpyridine catalyst couples N-alkyl pyridinium salts with in situ formed carboxylic acid fluorides or 2-pyridyl esters under reducing conditions (Mn metal). The reaction has a broad scope, as demonstrated by the synthesis of 35 different ketones bearing a wide variety of functional groups with an average yield of 60±16 %. This approach is capable of coupling diverse substrates, including pharmaceutical intermediates, to rapidly form complex ketones.
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