ArticleScience (New York, N.Y.)2018
Enantiodivergent Pd-catalyzed C-C bond formation enabled through ligand parameterization.
Article in Science (New York, N.Y.), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 54 papers.
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
54 citing papers in PubMed.
- Predicting the Reactivity of Acyclic Silylenes and Germylenes in Hydrogen Activation Using Machine Learning.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Practical Ni-Catalyzed Synthesis of Allylic Boronates.ACS omega · 2026Article
- Predicting Enantioselectivity of Ruthenium-Catalyzed Ketone Hydrogenation with 3D Structure-Based Deep Learning.Journal of the American Chemical Society · 2026Article
- Direct arylation polymerization of electron-rich arenes with polar-group tolerance enabled by ligand-coordination tuning.Chemical science · 2026Article
- Article
- Machine Learning in Homogeneous Catalysis: Basic Concepts and Best Practices.ACS catalysis · 2026Article
- Stereospecific cross-coupling reactions: Programmed assembly of chiral molecules by reaction of chiral reagents.Science advances · 2025Review
- Iridium-Catalyzed Stereocontrolled C(spJournal of the American Chemical Society · 2025Article
- Rapid prediction of conformationally-dependent DFT-level descriptors using graph neural networks for carboxylic acids and alkyl amines.Digital discovery · 2025Article
- Applying statistical modeling strategies to sparse datasets in synthetic chemistry.Science advances · 2025Review
- Article
- Rapid, Homogenous, B-Alkyl Suzuki-Miyaura Cross-Coupling of Boronic Esters.The Journal of organic chemistry · 2024Article
- Theoretical study on ligand conformational self-adaptation for modulating reactivity.Scientific reports · 2024Article
- Molecular complexity as a driving force for the advancement of organic synthesis.Nature reviews. Chemistry · 2024Review
- The current utility and future potential of multiborylated alkanes.Nature reviews. Chemistry · 2024Review
- Simultaneous Stereoinvertive and Stereoselective C(spJournal of the American Chemical Society · 2024Article
- Rational Design of Palladium(II) Indenyl and Allyl Complexes Bearing Phosphine and Isocyanide Ancillary Ligands with Promising Antitumor Activity.Molecules (Basel, Switzerland) · 2024Article
- Dataset Design for Building Models of Chemical Reactivity.ACS central science · 2023Review
- Visible light-induced palladium-carbon bond weakening in catalytically relevant T-shaped complexes.Chemical science · 2023Article
- Reactions of Benzylboronate Nucleophiles.Synthesis · 2023Article
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
Despite the enormous potential for the use of stereospecific cross-coupling reactions to rationally manipulate the three-dimensional structure of organic molecules, the factors that control the transfer of stereochemistry in these reactions remain poorly understood. Here we report a mechanistic and synthetic investigation into the use of enantioenriched alkylboron nucleophiles in stereospecific Pd-catalyzed Suzuki cross-coupling reactions. By developing a suite of molecular descriptors of phosphine ligands, we could apply predictive statistical models to select or design distinct ligands that respectively promoted stereoinvertive and stereoretentive cross-coupling reactions. Stereodefined branched structures were thereby accessed through the predictable manipulation of absolute stereochemistry, and a general model for the mechanism of alkylboron transmetallation was proposed.
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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.