ArticleACS catalysis2018
Nickel-Catalyzed Suzuki-Miyaura Coupling of Aliphatic Amides.
Article in ACS catalysis, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
- Mechanistic insights on C(acyl)-N functionalisation mediated by late transition metals.Dalton transactions (Cambridge, England : 2003) · 2024Review
- Skeletal metalation of lactams through a carbonyl-to-nickel-exchange logic.Nature communications · 2023Article
- Amide N-C Bond Activation: A Graphical Overview of Acyl and Decarbonylative Coupling.SynOpen (2017) · 2023Article
- Enabling Suzuki-Miyaura coupling of Lewis-basic arylboronic esters with a nonprecious metal catalyst.Chemical science · 2022Article
- Direct Dehydrogenative Access to Unsymmetrical Phenones.Angewandte Chemie (International ed. in English) · 2022Article
- Identifying the Imperative Role of Metal-Olefin Interactions in Catalytic C-O Reductive Elimination from Nickel(II).ACS catalysis · 2021Article
- Reductive Arylation of Amides via a Nickel-Catalyzed Suzuki-Miyaura-Coupling and Transfer-Hydrogenation Cascade.Angewandte Chemie (International ed. in English) · 2021Article
- Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.ACS catalysis · 2020Article
- Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids.Angewandte Chemie (International ed. in English) · 2020Article
- Organocatalytic asymmetric N-sulfonyl amide C-N bond activation to access axially chiral biaryl amino acids.Nature communications · 2020Article
- Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of Aliphatic Amides on the Benchtop.Organic letters · 2020Article
- Indolylboronic Acids: Preparation and Applications.Molecules (Basel, Switzerland) · 2019Review
- Breaking Amide C-N Bonds in an Undergraduate Organic Chemistry Laboratory.Journal of chemical education · 2019Article
- An Efficient, One-Pot Transamidation of 8-Aminoquinoline Amides Activated by Tertiary-Butyloxycarbonyl.Molecules (Basel, Switzerland) · 2019Article
- Chemoenzymatic conversion of amides to enantioenriched alcohols in aqueous medium.Communications chemistry · 2019Article
- Size-Dependent Catalytic Activity and Fate of Palladium Nanoparticles in Suzuki-Miyaura Coupling Reactions.ACS omega · 2018Article
- Computational Study of Mechanism and Thermodynamics of Ni/IPr-Catalyzed Amidation of Esters.Molecules (Basel, Switzerland) · 2018Article
- Palladium-Catalyzed Room Temperature Acylative Cross-Coupling of Activated Amides with Trialkylboranes.Molecules (Basel, Switzerland) · 2018Article
- Synthesis of Tetrasubstituted Alkenes by Tandem Metallacycle Formation/Cross-Electrophile Coupling.Journal of the American Chemical Society · 2018Article
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4 authors.
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Abstract
We report the Ni-catalyzed Suzuki-Miyaura coupling of aliphatic amide derivatives. Prior studies have shown that aliphatic amide derivatives can undergo Ni-catalyzed carbon-heteroatom bond formation but that Ni-mediated C-C bond formation using aliphatic amide derivatives has remained difficult. The coupling disclosed herein is tolerant of considerable variation with respect to both the amide-based substrate and the boronate coupling partner and proceeds in the presence of heterocycles and epimerizable stereocenters. Moreover, a gram-scale Suzuki-Miyaura coupling/Fischer indolization sequence demonstrates the ease with which unique polyheterocyclic scaffolds can be constructed, particularly by taking advantage of the enolizable ketone functionality present in the cross-coupled product. The methodology provides an efficient means to form C-C bonds from aliphatic amide derivatives using nonprecious-metal catalysis and offers a general platform for the heteroarylation of aliphatic acyl electrophiles.
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