ArticleJournal of the American Chemical Society2017
Structural, Kinetic, and Computational Characterization of the Elusive Arylpalladium(II)boronate Complexes in the Suzuki-Miyaura Reaction.
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 44 papers.
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Who cites it
44 citing papers in PubMed.
- Access to and unexplored reactivity of nickel-bound 5-membered O- and N-heterocyclic arynesChemical science · 2026Article
- Mechanism visualization of nanocluster catalysis via in situ mass spectrometry.Science advances · 2026Article
- Dual-Ligand System for Mild Decarbonylative Suzuki-Miyaura Cross-Coupling of Aroyl Chlorides.ACS catalysis · 2026Article
- From Boron to Bismuth: The Pre-transmetalation Complex in the Aryl Transfer.Journal of the American Chemical Society · 2026Article
- Analyzing the Solvent Effects in Palladium/The journal of physical chemistry. B · 2026Article
- Nickel-Catalyzed Efficient, Regioselective One-Pot Synthesis of 1-Methyleneindenes via Tandem C-C Bond Formation: Computational Mechanistic Insights and Docking Studies.Chemistry, an Asian journal · 2026Article
- Mechanistically Driven Development of Kumada Catalyst-Transfer Polymerizations: A Rapid Injection NMR Study.ACS catalysis · 2025Article
- Article
- Atomically Dispersed Palladium Promoted Suzuki-Miyaura Cross Coupling.ChemSusChem · 2025Article
- Suzuki-Miyaura Cross-Couplings: Juxtaposing the Transmetalation of Arylboronic Acids and Alkylboranes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Direct Observation of Alkyl Group Transmetalation from Boron to Copper: Impact of Structure Modification and the Critical Role of Copper-Oxygen Preassociation in Stereospecificity.Journal of the American Chemical Society · 2025Article
- Cyclization by Intramolecular Suzuki-Miyaura Cross-Coupling-A Review.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Synthesis and Suzuki-Miyaura Cross-Coupling of Alkyl Amine-Boranes. A Boryl Radical-Enabled Strategy.Journal of the American Chemical Society · 2024Article
- Halide Salts Alleviate TMSOK Inhibition in Suzuki-Miyaura Cross-Couplings.ACS catalysis · 2024Article
- Understanding and Controlling Reactivity Patterns of PdACS catalysis · 2024Article
- Phase transfer catalysts shift the pathway to transmetalation in biphasic Suzuki-Miyaura cross-couplings.Nature communications · 2024Article
- Nickel binding enables isolation and reactivity of previously inaccessible 7-aza-2,3-indolynes.Science (New York, N.Y.) · 2024Article
- ProPhos: A Ligand for Promoting Nickel-Catalyzed Suzuki-Miyaura Coupling Inspired by Mechanistic Insights into Transmetalation.Journal of the American Chemical Society · 2024Article
- Distinguishing Competing Mechanistic Manifolds for C(acyl)-N Functionalization by a Ni/JACS Au · 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
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Authors and funding
4 authors.
Funding
Abstract
The existence of the oft-invoked intermediates containing the crucial Pd-O-B subunit, the "missing link", has been established in the Suzuki-Miyaura cross-coupling reaction. The use of low-temperature, rapid injection NMR spectroscopy (RI-NMR), kinetic studies, and computational analysis has enabled the generation, observation, and characterization of these highly elusive species. The ability to confirm the intermediacy of Pd-O-B-containing species provided the opportunity to clarify mechanistic aspects of the transfer of the organic moiety from boron to palladium in the key transmetalation step. Specifically, these studies establish the identity of two different intermediates containing Pd-O-B linkages, a tri-coordinate (6-B-3) boronic acid complex and a tetra-coordinate (8-B-4) boronate complex, both of which undergo transmetalation leading to the cross-coupling product. Two distinct mechanistic pathways have been elucidated for stoichiometric reactions of these complexes: (1) transmetalation via an unactivated 6-B-3 intermediate that dominates in the presence of an excess of ligand, and (2) transmetalation via an activated 8-B-4 intermediate that takes place with a deficiency of ligand.
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