ArticleAngewandte Chemie (International ed. in English)2021
Coupling of Reformatsky Reagents with Aryl Chlorides Enabled by Ylide-Functionalized Phosphine Ligands.
Article in Angewandte Chemie (International ed. in English), 2021. 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.
- Harnessing Organopotassium Reagents for Cross-Coupling with YPhos-Pd Catalysts: Opportunities, Applications, and Challenges.Journal of the American Chemical Society · 2025Article
- Bulky, electron-rich, renewable: analogues of Beller's phosphine for cross-couplings.Catalysis science & technology · 2023Article
- Formation of exceptional monomeric YPhos-PdClChemical science · 2022Article
- Halogen-Bridged Methylnaphthyl Palladium Dimers as Versatile Catalyst Precursors in Coupling Reactions.Angewandte Chemie (International ed. in English) · 2021Article
- Synthesis, Crystal and Electronic Structures of a Thiophosphinoyl- and Amino-Substituted Metallated Ylide.ChemistryOpen · 2021Article
- Au⋅⋅⋅H-C Hydrogen Bonds as Design Principle in Gold(I) Catalysis.Angewandte Chemie (International ed. in English) · 2021Article
- Ylide-Substituted Phosphines with a Cyclic Ylide-Backbone: Angle Dependence of the Donor Strength.Organometallics · 2021Article
- Acceleration of 1,3-Dipolar Cycloadditions by Integration of Strain and Electronic Tuning.Journal of the American Chemical Society · 2021Article
- Coupling of Reformatsky Reagents with Aryl Chlorides Enabled by Ylide-Functionalized Phosphine Ligands.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
7 authors.
Funding
Abstract
The coupling of aryl chlorides with Reformatsky reagents is a desirable strategy for the construction of α-aryl esters but has so far been substantially limited in the substrate scope due to many challenges posed by various possible side reactions. This limitation has now been overcome by the tailoring of ylide-functionalized phosphines to fit the requirements of Negishi couplings. Record-setting activities were achieved in palladium-catalyzed arylations of organozinc reagents with aryl electrophiles using a cyclohexyl-YPhos ligand bearing an ortho-tolyl-substituent in the backbone. This highly electron-rich, bulky ligand enables the use of aryl chlorides in room temperature couplings of Reformatsky reagents. The reaction scope covers diversely functionalized arylacetic and arylpropionic acid derivatives. Aryl bromides and chlorides can be converted selectively over triflate electrophiles, which permits consecutive coupling strategies.
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