ArticleACS catalysis2019
Monophosphine Ligands Promote Pd-Catalyzed C-S Cross-Coupling Reactions at Room Temperature with Soluble Bases.
Article in ACS catalysis, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 87 citations in OpenAlex.
- A Modular Synthesis of C5-Sulfenyl Thiazoles via an Intermolecular Pummerer Rearrangement: An Underexplored Scaffold for Medicinal Chemistry.Angewandte Chemie (International ed. in English) · 2026Article
- Pd-Catalyzed O-Arylation of Phenols Mediated by a Weak, Soluble Organic Base: Methodology, Mechanism, and Compatibility with Enabling Technologies.Journal of the American Chemical Society · 2025Article
- C2-Selective Palladium-Catalyzed C-S Cross-Coupling of 2,4-Dihalopyrimidines.Journal of the American Chemical Society · 2025Article
- Data-driven discovery of active phosphine ligand space for cross-coupling reactions.Chemical science · 2024Article
- Phosphine-incorporated Metal-Organic Framework for Palladium Catalyzed Heck Coupling Reaction.ChemistryOpen · 2024Article
- Emerging Trends in Cross-Coupling: Twelve-Electron-Based LChemical reviews · 2022Review
- Forging C-S Bonds Through Decarbonylation: New Perspectives for the Synthesis of Privileged Aryl Sulfides.ChemCatChem · 2021Article
- Ni(II) Precatalysts Enable Thioetherification of (Hetero)Aryl Halides and Tosylates and Tandem C-S/C-N Couplings.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Development of an Aryl Amination Catalyst with Broad Scope Guided by Consideration of Catalyst Stability.Journal of the American Chemical Society · 2020Article
- Improved, Odorless Access to Benzo[1,2-d;4,5-d']- bis[1,3]dithioles andMolecules (Basel, Switzerland) · 2020Article
- Palladium nanoparticles immobilized on a nano-silica triazine dendritic polymer: a recyclable and sustainable nanoreactor for C-S cross-coupling.RSC advances · 2020Article
- The Quest for the Ideal Base: Rational Design of a Nickel Precatalyst Enables Mild, Homogeneous C-N Cross-Coupling.Journal of the American Chemical Society · 2020Article
Corrections and comments
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
Abstract
The Pd-catalyzed cross-coupling of thiols with aromatic electrophiles is a reliable method for the synthesis of aryl thioethers, which are important compounds for pharmaceutical and agricultural applications. Since thiols and thiolates strongly bind late transition metals, previous research has focused on catalysts supported by chelating, bisphosphine ligands, which were considered less likely to be displaced during the course of the reaction. We show that by using monophosphine ligands instead, more effective catalysis can be achieved. Notably, compared to previous methods, this increased reactivity allows for the use of much lower reaction temperature, soluble bases, and base-sensitive substrates. In contrast to conventional wisdom, our mechanistic data suggest that the extent of displacement of phosphine ligands by thiols is, firstly, not correlated with the ligand bulk or thiol nucleophilicity, and secondly, not predictive of the effectiveness of a given ligand in combination with palladium.
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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.