ArticleJournal of the American Chemical Society2019
Mechanism and Scope of Nickel-Catalyzed Decarbonylative Borylation of Carboxylic Acid Fluorides.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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28 citing papers in PubMed, 124 citations in OpenAlex.
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- Mechanistic insights into base-free nickel-catalyzed Suzuki-Miyaura cross-coupling of acid fluoride and the origin of chemoselectivity: a DFT study.RSC advances · 2025Article
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- Rapid Access to Carbon-Isotope-Labeled Alkyl and Aryl Carboxylates Applying Palladacarboxylates.JACS Au · 2023Article
- Mechanism-Driven Development of Group 10 Metal-Catalyzed Decarbonylative Coupling Reactions.Accounts of chemical research · 2022Article
- ElectrostaticChemical science · 2022Article
- Decarboxylative Borylation and Cross-Coupling of (Hetero)aryl Acids Enabled by Copper Charge Transfer Catalysis.Journal of the American Chemical Society · 2022Article
- Nucleophilic Fluorination Catalyzed by a Cyclometallated Rhodium Complex.Organometallics · 2022Article
- A C-to-O atom-swapping reaction sequence enabled by Ni-catalyzed decarbonylation of lactones.Chemical science · 2022Article
- Bulky Di(1-adamantyl)phosphinous Acid-Ligated Pd(II) Precatalysts for Suzuki Reactions of Unreactive Aryl Chlorides.ACS omega · 2021Article
- Direct synthesis and applications of solid silylzinc reagents.Chemical science · 2021Article
- Decarbonylative Fluoroalkylation at Palladium(II): From Fundamental Organometallic Studies to Catalysis.Journal of the American Chemical Society · 2021Article
- Ni-catalyzed hydroalkylation of olefins with N-sulfonyl amines.Nature communications · 2021Article
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4 authors at 1 institution in 1 country.
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Abstract
This Article describes the development of a base-free, nickel-catalyzed decarbonylative coupling of carboxylic acid fluorides with diboron reagents to selectively afford aryl boronate ester products. Detailed studies were conducted to assess the relative rates of direct transmetalation between aryl boronate esters and diboron reagents and a bisphosphine nickel(aryl)(fluoride) intermediate. These investigations revealed that diboron reagents undergo transmetalation with this Ni(aryl)(fluoride) intermediate at rates significantly faster than their aryl boronate ester congeners. Furthermore, the reactivity of both boron reagents toward transmetalation is enhanced with increasing electrophilicity of the boron center. These mechanistic insights were leveraged to develop a catalytic decarbonylative borylation of acid fluorides that proved applicable to a variety of (hetero)aryl carboxylic acid fluorides as well as diverse diboron reagents. The acid fluorides can be generated
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.