ArticleChemical science2021
Inhibition of (dppf)nickel-catalysed Suzuki-Miyaura cross-coupling reactions by α-halo-N-heterocycles.
Article in Chemical science, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Electronic and Steric Effects of the ProPhos Ligand Family for Nickel-Catalyzed Suzuki-Miyaura Coupling of Heteroaromatics.ACS catalysis · 2026Article
- Process-Ready Nickel-Catalyzed Suzuki-Miyaura Coupling Enabled byACS catalysis · 2025Article
- C(spAngewandte Chemie (International ed. in English) · 2025Article
- A Bench-Stable Fluorophosphine Nickel(0) Complex and Its Catalytic Application.Angewandte Chemie (International ed. in English) · 2025Article
- Efficient Nickel Precatalysts for Suzuki-Miyaura Cross-Coupling of Aryl Chlorides and Arylboronic Acids Under Mild Conditions.Angewandte Chemie (International ed. in English) · 2025Article
- "Naked Nickel"-Catalyzed Heteroaryl-Heteroaryl Suzuki-Miyaura Coupling.Angewandte Chemie (International ed. in English) · 2025Article
- ProPhos: A Ligand for Promoting Nickel-Catalyzed Suzuki-Miyaura Coupling Inspired by Mechanistic Insights into Transmetalation.Journal of the American Chemical Society · 2024Article
Corrections and comments
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Authors and funding
7 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
A nickel/dppf catalyst system was found to successfully achieve the Suzuki-Miyaura cross-coupling reactions of 3- and 4-chloropyridine and of 6-chloroquinoline but not of 2-chloropyridine or of other α-halo-N-heterocycles. Further investigations revealed that chloropyridines undergo rapid oxidative addition to [Ni(COD)(dppf)] but that α-halo-N-heterocycles lead to the formation of stable dimeric nickel species that are catalytically inactive in Suzuki-Miyaura cross-coupling reactions. However, the corresponding Kumada-Tamao-Corriu reactions all proceed readily, which is attributed to more rapid transmetalation of Grignard reagents.
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