ArticleJournal of the American Chemical Society2020
Development of an Aryl Amination Catalyst with Broad Scope Guided by Consideration of Catalyst Stability.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed, 78 citations in OpenAlex.
- Ligand-enabled next-generation glycosyl Stille cross-coupling for the stereospecific synthesis of sterically hindered aryl C-glycosides.Nature communications · 2026Article
- Synthesis of Anthraquinone Mono- and Diboron Complexes with Near-Infrared Panchromatic Absorption.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- C(spJournal of the American Chemical Society · 2025Article
- Precise synthesis of advanced polyarylamines for efficient perovskite solar cells.Nature materials · 2025Article
- Mechanochemical Generation of Active Pd/BippyPhos Catalyst for Efficient CN Cross-Coupling in Air.ChemSusChem · 2025Article
- Recent Green and Sustainable Pd-Catalyzed Aminations.ChemSusChem · 2025Review
- Article
- Cross-Coupling Reactions with Nickel, Visible Light, andACS catalysis · 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
- Palladium-Catalyzed Amination of Aryl Halides with Aqueous Ammonia and Hydroxide Base Enabled by Ligand Development.Journal of the American Chemical Society · 2024Article
- Article
- Nanoparticles asACS sustainable chemistry & engineering · 2024Article
- Room-Temperature Cu-Catalyzed Amination of Aryl Bromides Enabled by DFT-Guided Ligand Design.Journal of the American Chemical Society · 2023Article
- Important Role of NH-Carbazole in Aryl Amination Reactions Catalyzed by 2-Aminobiphenyl Palladacycles.ACS catalysis · 2023Article
- Pd-Catalyzed Amination of Base-Sensitive Five-Membered Heteroaryl Halides with Aliphatic Amines.Journal of the American Chemical Society · 2023Article
- Emerging Trends in Cross-Coupling: Twelve-Electron-Based LChemical reviews · 2022Review
- Sterically Controlled Late-Stage Functionalization of Bulky Phosphines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Cooperative Hydrogen-Bond-Donor Catalysis with Hydrogen Chloride Enables Highly Enantioselective Prins Cyclization Reactions.Journal of the American Chemical Society · 2021Article
- GPhos Ligand Enables Production of Chiral N-Arylamines in a Telescoped Transaminase-Buchwald-Hartwig Amination Cascade in the Presence of Excess Amine Donor.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
We have developed a new dialkylbiaryl monophosphine ligand, GPhos, that supports a palladium catalyst capable of promoting carbon-nitrogen cross-coupling reactions between a variety of primary amines and aryl halides; in many cases, these reactions can be carried out at room temperature. The reaction development was guided by the idea that the productivity of catalysts employing BrettPhos-like ligands is limited by their lack of stability at room temperature. Specifically, it was hypothesized that primary amine and N-heteroaromatic substrates can displace the phosphine ligand, leading to the formation of catalytically dormant palladium complexes that reactivate only upon heating. This notion was supported by the synthesis and kinetic study of a putative off-cycle Pd complex. Consideration of this off-cycle species, together with the identification of substrate classes that are not effectively coupled at room temperature using previous catalysts, led to the design of a new dialkylbiaryl monophosphine ligand. An O
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.