ArticleJournal of the American Chemical Society2017
Mechanistic Study of an Improved Ni Precatalyst for Suzuki-Miyaura Reactions of Aryl Sulfamates: Understanding the Role of Ni(I) Species.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 47 papers.
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Who cites it
47 citing papers in PubMed.
- Kinetic Analysis of Transmetalation at Prototypical NickelAngewandte Chemie (International ed. in English) · 2026Article
- Pincer Nickel(II) Catalyzed Oxidative Carbonylation of Amines: A Phosgene-Free Synthesis for Isocyanates and Ureas.ACS omega · 2026Article
- Controlling the Redox Speciation of N,C,N-Bi Complexes Using the Anion Coordination Index.Organometallics · 2026Article
- Process-Ready Nickel-Catalyzed Suzuki-Miyaura Coupling Enabled byACS catalysis · 2025Article
- Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction of Aliphatic Alcohol Derivatives.Angewandte Chemie (International ed. in English) · 2025Article
- "Naked Nickel"-Catalyzed Heteroaryl-Heteroaryl Suzuki-Miyaura Coupling.Angewandte Chemie (International ed. in English) · 2025Article
- "Naked Nickel"-Catalyzed Amination of Heteroaryl Bromides.Organic letters · 2024Article
- Isolation and Reactivity of Arylnickel(II) Complexes in Nickel-Catalyzed Borylation of Aryl Fluorosulfates.JACS Au · 2024Article
- ProPhos: A Ligand for Promoting Nickel-Catalyzed Suzuki-Miyaura Coupling Inspired by Mechanistic Insights into Transmetalation.Journal of the American Chemical Society · 2024Article
- Synthesis of Nickel(I)-Bromide Complexes via Oxidation and Ligand Displacement: Evaluation of Ligand Effects on Speciation and Reactivity.Journal of the American Chemical Society · 2023Article
- Ni-Catalyzed Enantioselective Intramolecular Mizoroki-Heck Reaction for the Synthesis of Phenanthridinone Derivatives.The Journal of organic chemistry · 2023Article
- 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
- Homogeneous Organic Electron Donors in Nickel-Catalyzed Reductive Transformations.The Journal of organic chemistry · 2022Review
- DFT insight into asymmetric alkyl-alkyl bond formationChemical science · 2022Article
- Non-CMolecules (Basel, Switzerland) · 2021Article
- Mechanistic Aspects of the Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling Reaction.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters.Journal of the American Chemical Society · 2021Article
- Highly economical and direct amination of spRSC advances · 2021Article
- A Widely Applicable Dual Catalytic System for Cross-Electrophile Coupling Enabled by Mechanistic Studies.ACS catalysis · 2020Article
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8 authors.
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Abstract
Nickel precatalysts are potentially a more sustainable alternative to traditional palladium precatalysts for the Suzuki-Miyaura coupling reaction. Currently, there is significant interest in Suzuki-Miyaura coupling reactions involving readily accessible phenolic derivatives such as aryl sulfamates, as the sulfamate moiety can act as a directing group for the prefunctionalization of the aromatic backbone of the electrophile prior to cross-coupling. By evaluating complexes in the Ni(0), (I), and (II) oxidation states we report a precatalyst, (dppf)Ni(o-tolyl)(Cl) (dppf = 1,1'-bis(diphenylphosphino)ferrocene), for Suzuki-Miyaura coupling reactions involving aryl sulfamates and boronic acids, which operates at a significantly lower catalyst loading and at milder reaction conditions than other reported systems. In some cases it can even function at room temperature. Mechanistic studies on precatalyst activation and the speciation of nickel during catalysis reveal that Ni(I) species are formed in the catalytic reaction via two different pathways: (i) the precatalyst (dppf)Ni(o-tolyl)(Cl) undergoes comproportionation with the active Ni(0) species; and (ii) the catalytic intermediate (dppf)Ni(Ar)(sulfamate) (Ar = aryl) undergoes comproportionation with the active Ni(0) species. In both cases the formation of Ni(I) is detrimental to catalysis, which is proposed to proceed via a Ni(0)/Ni(II) cycle. DFT calculations are used to support experimental observations and provide insight about the elementary steps involved in reactions directly on the catalytic cycle, as well as off-cycle processes. Our mechanistic investigation provides guidelines for designing even more active nickel catalysts.
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