ArticleJournal of the American Chemical Society2017
Mechanistic Investigations of the Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Benzyl Acrylates.
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 32 papers.
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Who cites it
32 citing papers in PubMed.
- Synergistic Fe/Ni catalysis for electrochemical 1,1-difunctionalization of alkenes.Nature communications · 2026Article
- Palladium-catalyzed asymmetric migratory diarylation of unactivated directing-group-free internal alkenes.Nature communications · 2026Article
- Studying Noncovalent Interactions in Molecular Systems with Machine Learning.Chemical reviews · 2025Review
- Machine-Learning-Based Design of Metallocene Catalysts for Controlled Olefin Copolymerization.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Design Approaches That Utilize Ionic Interactions to Control Selectivity in Transition Metal Catalysis.Chemical reviews · 2025Review
- Selective Ni(I)/Ni(III) Process for Consecutive Geminal C(spJournal of the American Chemical Society · 2024Article
- Asymmetric Migratory Tsuji-Wacker Oxidation Enables the Enantioselective Synthesis of Hetero- and Isosteric Diarylmethanes.Journal of the American Chemical Society · 2024Article
- Fe-Catalyzed Fluoroalkyl(hetero)arylation of Vinyl Azaarenes: Rapid and Modular Synthesis of Unsymmetrical 1,1-Bis(hetero)arylalkanes.Organic letters · 2024Article
- Catalysing (organo-)catalysis: Trends in the application of machine learning to enantioselective organocatalysis.Beilstein journal of organic chemistry · 2024Review
- Article
- Nickel-Catalyzed 1,1-Aminoborylation of Unactivated Terminal Alkenes.ACS catalysis · 2023Article
- α-Branched amines through radical coupling with 2-azaallyl anions, redox active esters and alkenes.Chemical science · 2022Article
- Palladium-catalyzed 1,1-alkynylbromination of alkenes with alkynyl bromides.Chemical science · 2021Article
- Nickel-Catalyzed Regioselective Alkenylarylation of γ,δ-Alkenyl Ketones via Carbonyl Coordination.Angewandte Chemie (International ed. in English) · 2021Article
- Organozinc pivalates for cobalt-catalyzed difluoroalkylarylation of alkenes.Nature communications · 2021Article
- Photoinduced 1,2-dicarbofunctionalization of alkenes with organotrifluoroborate nucleophilesChemical science · 2021Article
- Walking metals: catalytic difunctionalization of alkenes at nonclassical sites.Chemical science · 2020Review
- Nickel-Catalyzed α-Carbonylalkylarylation of Vinylarenes: Expedient Access to γ,γ-Diarylcarbonyl and Aryltetralone Derivatives.Angewandte Chemie (International ed. in English) · 2020Article
- Recent applications of chiral phosphoric acids in palladium catalysis.Organic & biomolecular chemistry · 2020Review
- Internal acidity scale and reactivity evaluation of chiral phosphoric acids with different 3,3'-substituents in Brønsted acid catalysis.Chemical science · 2019Article
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5 authors.
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Abstract
A mechanistic study of the Pd-catalyzed enantioselective 1,1-diarylation of benzyl acrylates that is facilitated by a chiral anion phase transfer (CAPT) process is presented. Kinetic analysis, labeling, competition, and nonlinear effect experiments confirm the hypothesized general mechanism and reveal the role of the phosphate counterion in the CAPT catalysis. The phosphate was found to be involved in the phase transfer step and in the stereoinduction process, as expected, but also in the unproductive reaction that provides the traditional Heck byproduct. Multivariate correlations revealed the CAPT catalyst's structural features, affecting the production of this undesired byproduct, as well as weak interactions responsible for enantioselectivity. Such putative interactions include π-stacking and a CH···O electrostatic attraction between the substrate benzyl moiety and the phosphate. Analysis of the computed density functional theory transition structures for the stereodetermining step of the reaction supports the multivariate model obtained. The presented work provides the first comprehensive study of the combined use of CAPT and transition metal catalysis, setting the foundation for future applications.
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