ArticleJournal of the American Chemical Society2012
Mechanistic investigation of the nickel-catalyzed Suzuki reaction of N,O-acetals: evidence for boronic acid assisted oxidative addition and an iminium activation pathway.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed, 76 citations in OpenAlex.
- DiploPhos: A Hemilabile Bisphosphine for Sterically Hindered Ni-Catalyzed Suzuki-Miyaura Couplings.ACS catalysis · 2026Article
- Copper-Catalyzed Petasis-Type Reaction Enables Efficient Synthesis of C1-Substituted Tetrahydro-β-carbolines.Organic letters · 2026Article
- Strategies for the Development of Asymmetric and Non-Directed Petasis Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Enantioselective Synthesis of Sealutomicin C.Journal of the American Chemical Society · 2024Article
- Metal-Catalyzed Enantioconvergent Transformations.Chemical reviews · 2023Review
- Kinetic Resolution of 2-Aryldihydroquinolines Using Lithiation - Synthesis of Chiral 1,2- and 1,4-Dihydroquinolines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Enantioselective Hydroalkoxylation of 1,3-Dienes via Ni-Catalysis.Journal of the American Chemical Society · 2023Article
- Late-StageJournal of the American Chemical Society · 2021Article
- UsingInorganic chemistry · 2021Article
- Ultrasound-Assisted Hydrazine Reduction Method for the Preparation of Nickel Nanoparticles, Physicochemical Characterization and Catalytic Application in Suzuki-Miyaura Cross-Coupling Reaction.Nanomaterials (Basel, Switzerland) · 2020Article
- Copper-catalyzed oxidative cross-dehydrogenative coupling of 2H-chromenes and terminal alkynes.Organic & biomolecular chemistry · 2018Article
- Ni-Catalyzed Carbon-Carbon Bond-Forming Reductive Amination.Journal of the American Chemical Society · 2018Article
- Dual nickel and Lewis acid catalysis for cross-electrophile coupling: the allylation of aryl halides with allylic alcohols.Chemical science · 2018Article
- Mechanism and Origins of Ligand-Controlled Stereoselectivity of Ni-Catalyzed Suzuki-Miyaura Coupling with Benzylic Esters: A Computational Study.Journal of the American Chemical Society · 2017Article
- Parameterization of phosphine ligands demonstrates enhancement of nickel catalysis via remote steric effects.Nature chemistry · 2017Article
- Kinetic resolution of racemic 2-substituted 1,2-dihydroquinolinesChemical science · 2017Article
- Mechanistic Study of an Improved Ni Precatalyst for Suzuki-Miyaura Reactions of Aryl Sulfamates: Understanding the Role of Ni(I) Species.Journal of the American Chemical Society · 2017Article
- Nickel-Catalyzed C-3 Direct Arylation of Pyridinium Ions for the Synthesis of 1-Azafluorenes.Chemical science · 2016Article
- Nickel-catalyzed enantioselective arylation of pyridine.Chemical science · 2016Article
- Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.Chemical reviews · 2015Review
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The mechanism of a recently reported Suzuki coupling reaction of quinoline-derived allylic N,O-acetals has been studied using a combination of structural, stereochemical, and kinetic isotope effect experiments. The data indicate that C-O activation is facilitated by Lewis acid assistance from the boronic acid coupling partner and an ionic S(N)1-like mechanism accounts for oxidative addition. In this context, we demonstrate the first direct observation of oxidative addition to a quinolinium salt. Notably, this mechanism is distinct from the more commonly described S(N)2(')-type oxidative addition of low-valent transition metals to most allylic electrophiles.
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Registered trials
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.