ArticleJournal of the American Chemical Society2018
Overcoming the Limitations of γ- and δ-C-H Arylation of Amines through Ligand Development.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 52 papers.
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Who cites it
52 citing papers in PubMed.
- Conformation-driven C3-C(Nature catalysis · 2026Article
- Deaminative Giese-type reaction.Nature chemistry · 2025Article
- From Mono-Accounts of chemical research · 2025Review
- Divergent Kinetic/Thermodynamic Selectivity in Palladium(II)-Mediated C-H Activation to Form 5- and 6-Membered Palladacycles.Journal of the American Chemical Society · 2025Article
- Palladium-Catalyzed Methylene β-C-H Fluorination of Native Amides.Journal of the American Chemical Society · 2025Article
- Palladium catalyzed ortho-C(spNature communications · 2024Article
- 2-Bromopyridines as Versatile Synthons for Heteroarylated 2-Pyridones via Ru(II)-Mediated Domino C-O/C-N/C-C Bond Formation Reactions.Molecules (Basel, Switzerland) · 2024Article
- Palladium (II)-Catalyzed C-H Activation with Bifunctional Ligands: From Curiosity to Industrialization.Angewandte Chemie (International ed. in English) · 2024Review
- Synthesis of Highly Substituted Aminotetrahydropyrans Enabled by Stereospecific Multivector C-H Functionalization.Organic letters · 2024Article
- Palladium-CatalyzedMolecules (Basel, Switzerland) · 2024Article
- Ligand-Enabled Double γ-C(spAngewandte Chemie (International ed. in English) · 2023Article
- Dual Copper- and Aldehyde-Catalyzed Transient C-H Sulfonylation of Benzylamines.Organic letters · 2023Article
- Article
- β- and γ-C(spAngewandte Chemie (International ed. in English) · 2023Article
- Directed Photochemically Mediated Nickel-Catalyzed (Hetero)arylation of Aliphatic C-H Bonds.Journal of the American Chemical Society · 2023Article
- Multiple remote C(spChemical science · 2022Article
- PdACS catalysis · 2022Article
- Ligand-Enabled β-C(spAngewandte Chemie (International ed. in English) · 2022Article
- One-Step Synthesis of β-Alkylidene-γ-lactones via Ligand-Enabled β,γ-Dehydrogenation of Aliphatic Acids.Journal of the American Chemical Society · 2022Article
- δ-C-H Halogenation Reactions Enabled by a Nitrogen-Centered Radical Precursor.Organic letters · 2022Article
Corrections and comments
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Authors and funding
8 authors.
Funding
Abstract
L,X-Type transient directing groups (TDGs) based on a reversible imine linkage have emerged as broadly useful tools for C-H activation of ketones and free amines. However, competitive binding interactions among multiple reaction components (TDG itself, substrate, and substrate-TDG adduct) with the palladium catalyst often lead to the formation of multiple unreactive complexes, rendering ligand development extremely challenging. Herein, we report the finding of versatile 2-pyridone ligands that addresses these problems and significantly improves the γ-methylene arylation of alkyl amines, extending the coupling partners to a wide range of medicinally important heteroaryl iodides and even previously unreactive heteroaryl bromides. The combination of an appropriate transient directing group and pyridone ligand has also enabled the δ-arylation of alkyl amines. Notably, our transient directing group design reveals the importance of matching the size of the Pd-chelation with different transient directing groups and the size of palladacycles generated from γ- and δ-C-H bonds: TDGs that coordinate with Pd(II) to form a six-membered chelate are selective toward γ-C-H bonds, whereas TDGs that coordinate with Pd(II) via a five-membered chelate tend to activate δ-C-H bonds. These findings provide an avenue for developing protecting group free and selective C-H functionalization using the transient directing group strategy.
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Registered trials
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