ArticleJournal of the American Chemical Society2016
Biaryl Phosphine Based Pd(II) Amido Complexes: The Effect of Ligand Structure on Reductive Elimination.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed.
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- Ligand-enabled next-generation glycosyl Stille cross-coupling for the stereospecific synthesis of sterically hindered aryl C-glycosides.Nature communications · 2026Article
- Chiral Imidazo[1,5‑JACS Au · 2025Article
- Pd-Catalyzed O-Arylation of Phenols Mediated by a Weak, Soluble Organic Base: Methodology, Mechanism, and Compatibility with Enabling Technologies.Journal of the American Chemical Society · 2025Article
- Kinetic Modeling Enables Understanding of Off-Cycle Processes in Pd-Catalyzed Amination of Five-Membered Heteroaryl Halides.Journal of the American Chemical Society · 2024Article
- Development of a Deactivation-Resistant Dialkylbiarylphosphine Ligand for Pd-Catalyzed Arylation of Secondary Amines.Journal of the American Chemical Society · 2024Article
- Investigating the Origin of Epimerization Attenuation during Pd-Catalyzed Cross-Coupling Reactions.ACS catalysis · 2024Article
- Design and Synthesis of Dialkylarylphosphine Urea Ligands and their Application in Palladium-Catalyzed Cross-Coupling Reactions.Helvetica chimica acta · 2024Article
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- Pd-Catalyzed Amination of Base-Sensitive Five-Membered Heteroaryl Halides with Aliphatic Amines.Journal of the American Chemical Society · 2023Article
- Ring walking as a regioselectivity control element in Pd-catalyzed C-N cross-coupling.Nature communications · 2022Article
- A Ligand Exchange Process for the Diversification of Palladium Oxidative Addition Complexes.Organic letters · 2021Article
- Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki-Miyaura Reactions of Diarylmethyl Esters.Organometallics · 2021Article
- Crystal structure of the RuPhos ligand.Acta crystallographica. Section E, Crystallographic communications · 2021Article
- Aryl Amination Using Soluble Weak Base Enabled by a Water-Assisted Mechanism.Journal of the American Chemical Society · 2020Article
- Development of an Aryl Amination Catalyst with Broad Scope Guided by Consideration of Catalyst Stability.Journal of the American Chemical Society · 2020Article
- Article
- Visible-Light-Enabled Direct Decarboxylative N-Alkylation.Angewandte Chemie (International ed. in English) · 2020Article
- Mechanistic Studies of the Palladium-Catalyzed Desulfinative Cross-Coupling of Aryl Bromides and (Hetero)Aryl Sulfinate Salts.Journal of the American Chemical Society · 2020Article
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Abstract
Kinetic studies conducted under both catalytic and stoichiometric conditions were employed to investigate the reductive elimination of RuPhos (2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl) based palladium amido complexes. These complexes were found to be the resting state in Pd-catalyzed cross-coupling reactions for a range of aryl halides and diarylamines. Hammett plots demonstrated that Pd(II) amido complexes derived from electron-deficient aryl halides or electron-rich diarylamines undergo faster rates of reductive elimination. A Hammett study employing SPhos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl) and analogues of SPhos demonstrated that electron donation of the "lower" aryl group is key to the stability of the amido complex with respect to reductive elimination. The rate of reductive elimination of an amido complex based on a BrettPhos-RuPhos hybrid ligand (2-(dicyclohexylphosphino)-3,6-dimethoxy-2',6'-diisopropoxybiphenyl) demonstrated that the presence of the 3-methoxy substituent on the "upper" ring of the ligand slows the rate of reductive elimination. These studies indicate that reductive elimination occurs readily for more nucleophilic amines such as N-alkyl anilines, N,N-dialkyl amines, and primary aliphatic amines using this class of ligands.
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