ArticleChemical science2019
Palladium-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of amides by carbon-nitrogen bond activation.
Article in Chemical science, 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.
- High-Sensitivity Sensor for Palladium Detection in Organic Solvent.International journal of molecular sciences · 2025Article
- Pd-Catalyzed Decarbonylative Suzuki-Miyaura Cross-Coupling of Pyramidalized N-Mesyl Amides by a Tandem N-C(O)/C-C Bond Activation.The Journal of organic chemistry · 2024Article
- Mechanistic insights on C(acyl)-N functionalisation mediated by late transition metals.Dalton transactions (Cambridge, England : 2003) · 2024Review
- Hypervalent iodine-promoted twofold oxidative coupling of amines with amides and thioamides: chemoselective pathway to oxazoles and thiazoles.Chemical science · 2023Article
- Divergent Acyl and Decarbonylative Liebeskind-Srogl Cross-Coupling of Thioesters by Cu-Cofactor and Pd-NHC (NHC = N-Heterocyclic Carbene) Catalysis.ACS catalysis · 2023Article
- Amide N-C Bond Activation: A Graphical Overview of Acyl and Decarbonylative Coupling.SynOpen (2017) · 2023Article
- Transition-metal-catalyzed synthesis of quinazolines: A review.Frontiers in chemistry · 2023Review
- Decarbonylative Pd-Catalyzed Suzuki Cross-Coupling for the Synthesis of Structurally Diverse Heterobiaryls.Organic letters · 2022Article
- Cu(i) catalysis for selective condensation/bicycloaromatization of two different arylalkynes: direct and general construction of functionalized C-N axial biaryl compounds.Chemical science · 2021Article
- Bulky Di(1-adamantyl)phosphinous Acid-Ligated Pd(II) Precatalysts for Suzuki Reactions of Unreactive Aryl Chlorides.ACS omega · 2021Article
- Mechanistic Aspects of the Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Enterovirus Inhibition by Hinged Aromatic Compounds with Polynuclei.Molecules (Basel, Switzerland) · 2020Article
- Decarbonylative Suzuki-Miyaura Cross-Coupling of Aroyl Chlorides.Organic letters · 2020Article
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Authors and funding
4 authors.
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Abstract
Palladium-catalyzed Suzuki-Miyaura cross-coupling or aryl halides is widely employed in the synthesis of many important molecules in synthetic chemistry, including pharmaceuticals, polymers and functional materials. Herein, we disclose the first palladium-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of amides for the synthesis of biaryls through the selective activation of the N-C(O) bond of amides. This new method relies on the precise sequence engineering of the catalytic cycle, wherein decarbonylation occurs prior to the transmetallation step. The reaction is compatible with a wide range of boronic acids and amides, providing valuable biaryls in high yields (>60 examples). DFT studies support a mechanism involving oxidative addition, decarbonylation and transmetallation and provide insight into high N-C(O) bond activation selectivity. Most crucially, the reaction establishes the use of palladium catalysis in the biaryl Suzuki-Miyaura cross-coupling of the amide bond and should enable the design of a wide variety of cross-coupling methods in which palladium rivals the traditional biaryl synthesis from aryl halides and pseudohalides.
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