ArticleJournal of the American Chemical Society2024
Development of a Deactivation-Resistant Dialkylbiarylphosphine Ligand for Pd-Catalyzed Arylation of Secondary Amines.
Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Integration of palladium-catalyzed C-N coupling into self-encoded libraries for accelerated hit discovery.RSC chemical biology · 2026Article
- Conjugation Lock-In Reinforced Sulfur-Heteropolycyclic Covalent Organic Frameworks with Asymmetric Electron Distribution for Photocatalytic Aerobic Oxidation Reactions.Journal of the American Chemical Society · 2026Article
- Ligand-enabled next-generation glycosyl Stille cross-coupling for the stereospecific synthesis of sterically hindered aryl C-glycosides.Nature communications · 2026Article
- Enantiotopic-group-selective coupling for unified access to carbazole atropisomers as versatile chiral chromophores.Nature communications · 2025Article
- Synthesis andOrganic letters · 2025Article
- Development of a Ligand for Cu-Catalyzed Amination of Base-Sensitive (Hetero)aryl Chlorides.Journal of the American Chemical Society · 2025Article
- Deciphering the Synchronization of Alternating Current Frequency with the Nickel Catalytic Cycle in Selective C-N Cross-Coupling.Journal of the American Chemical Society · 2025Article
- A database of steric and electronic properties of heteroaryl substituents.Scientific data · 2025Article
- Nickel catalyzed C-N coupling of haloarenes with BNature communications · 2025Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
Despite the prevalence of N-heteroarenes in small-molecule pharmaceuticals, Pd-catalyzed C-N cross-coupling reactions of aryl halides and amines containing these rings remain challenging due to their ability to displace the supporting ligand via coordination to the metal center. To address this limitation, we report the development of a highly robust Pd catalyst supported by a new dialkylbiarylphosphine ligand, FPhos. The FPhos-supported catalyst effectively resists N-heteroarene-mediated catalyst deactivation to readily promote C-N coupling between a wide variety of Lewis-basic aryl halides and secondary amines, including densely functionalized pharmaceuticals. Mechanistic and structural investigations, as well as principal component analysis and density functional theory, elucidated two key design features that enable FPhos to overcome the limitations of previous ligands. First, the ligated Pd complex is stabilized through its conformational preference for the O-bound isomer, which likely resists coordination by N-heteroarenes. Second, 3',5'-disubstitution on the non-phosphorus-containing ring of FPhos creates the ideal steric environment around the Pd center, which facilitates binding by larger secondary amines while mitigating the formation of off-cycle palladacycle species.
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Registered trials
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