ArticleAngewandte Chemie (International ed. in English)2017
Mechanistic Insight Leads to a Ligand Which Facilitates the Palladium-Catalyzed Formation of 2-(Hetero)Arylaminooxazoles and 4-(Hetero)Arylaminothiazoles.
Article in Angewandte Chemie (International ed. in English), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- Ligand-enabled next-generation glycosyl Stille cross-coupling for the stereospecific synthesis of sterically hindered aryl C-glycosides.Nature communications · 2026Article
- An active representation learning method for reaction yield prediction with small-scale data.Communications chemistry · 2025Article
- Development of a Deactivation-Resistant Dialkylbiarylphosphine Ligand for Pd-Catalyzed Arylation of Secondary Amines.Journal of the American Chemical Society · 2024Article
- Synthesis of 5-(Aryl)amino-1,2,3-triazole-containing 2,1,3-Benzothiadiazoles via Azide-Nitrile Cycloaddition Followed by Buchwald-Hartwig Reaction.Molecules (Basel, Switzerland) · 2024Article
- Predicting success in Cu-catalyzed C-N coupling reactions using data science.Science advances · 2024Article
- 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
- Development of an Aryl Amination Catalyst with Broad Scope Guided by Consideration of Catalyst Stability.Journal of the American Chemical Society · 2020Article
- 2-Aminooxazole as a Novel Privileged Scaffold in Antitubercular Medicinal Chemistry.ACS medicinal chemistry letters · 2020Article
- An Improved PJournal of the American Chemical Society · 2020Article
- Unexpected Formation of Hexasubstituted Arenes through a 2-fold Palladium-Mediated Ligand Arylation.The Journal of organic chemistry · 2019Article
- Biaryl Monophosphine Ligands in Palladium-Catalyzed C-N Coupling: An Updated User's Guide.Tetrahedron · 2019Article
- Pd-Catalyzed C-N Coupling Reactions Facilitated by Organic Bases: Mechanistic Investigation Leads to Enhanced Reactivity in the Arylation of Weakly Binding Amines.ACS catalysis · 2019Article
- Breaking the Base Barrier: An Electron-Deficient Palladium Catalyst Enables the Use of a Common Soluble Base in C-N Coupling.Journal of the American Chemical Society · 2018Article
- Organic synthesis provides opportunities to transform drug discovery.Nature chemistry · 2018Review
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3 authors.
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Abstract
By using mechanistic insight, a new ligand (EPhos) for the palladium-catalyzed C-N cross-coupling between primary amines and aryl halides has been developed. Employing an isopropoxy group at the C3-position favors the C-bound isomer of the ligand-supported palladium(II) complexes and leads to significantly improved reactivity. The use of a catalyst system based on EPhos with NaOPh as a mild homogeneous base proved to be very effective in the formation of 4-arylaminothiazoles and highly functionalized 2-arylaminooxazoles. Previously, these were not readily accessible using palladium catalysis.
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