ArticleOrganometallics2019
Bis(dialkylphosphino)ferrocene-Ligated Nickel(II) Precatalysts for Suzuki-Miyaura Reactions of Aryl Carbonates.
Article in Organometallics, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Controlling the Redox Speciation of N,C,N-Bi Complexes Using the Anion Coordination Index.Organometallics · 2026Article
- Article
- Discovery of NiJournal of the American Chemical Society · 2025Article
- Comparison of Monophosphine and Bisphosphine Precatalysts for Ni-Catalyzed Suzuki-Miyaura Cross-Coupling: Understanding the Role of the Ligation State in Catalysis.ACS catalysis · 2023Article
- Elucidating electron-transfer events in polypyridine nickel complexes for reductive coupling reactions.Nature catalysis · 2023Article
- 2,2-difluorovinyl benzoates for diverse synthesis of gem-difluoroenol ethers by Ni-catalyzed cross-coupling reactions.Nature communications · 2021Article
- Ligand Steric Effects of α-Diimine Nickel(II) and Palladium(II) Complexes in the Suzuki-Miyaura Cross-Coupling Reaction.ACS omega · 2020Article
- Unexpected Nickel Complex Speciation Unlocks Alternative Pathways for the Reactions of Alkyl Halides with dppf-Nickel(0).ACS catalysis · 2020Article
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Authors and funding
11 authors.
Funding
Abstract
Aryl carbonates, a common protecting group in synthetic organic chemistry, are potentially valuable electrophiles in cross-coupling reactions. Here, after performing a thorough evaluation of different precatalysts, we demonstrate that (dcypf)Ni(2-ethylphenyl)(Br) (dcypf = 1,1-bis-(dicyclohexylphosphino)ferrocene) is an efficient precatalyst for Suzuki-Miyaura reactions using a variety of aryl carbonates as substrates. Mechanistic studies indicate that (dcypf)Ni(2-ethylphenyl)(Br), which contains a bidentate phosphine that binds in a trans geometry, is an effective precatalyst for these reactions for two reasons: (i) it rapidly forms the Ni(O) active species and (ii) it minimizes comproportionation reactions between the Ni(O) active species and both the unactivated Ni(II) precatalyst and on-cycle Ni(II) complexes to form catalytically inactive Ni(I) species. In contrast, the state of the art precatalyst (dppf)Ni(
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