ArticleNature communications2021
Pd-catalyzed formal Mizoroki-Heck coupling of unactivated alkyl chlorides.
Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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Who cites it
34 citing papers in PubMed.
- Redox-neutral ketone-olefin coupling enabled by mild ketone-to-ketyl-type radical conversion.Nature chemistry · 2026Article
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- Low-Energy Light-Driven Excited-State Palladium Catalysis: Cross-Coupling of PyridineOrganic letters · 2026Article
- Stereodivergent synthesis of chiral amines bearing vicinal stereocenters via hydroamination of trisubstituted alkenes.Nature communications · 2026Article
- Article
- Cobaloxime Catalysis: A General Platform for Mizoroki-Heck-Type Reactions and Catalytic Dehydrohalogenations of Unactivated Alkyl Chlorides.Journal of the American Chemical Society · 2026Article
- Virtual Ligand-Assisted Screening for the Generation of Ketyl Radicals from Alkyl Ketones via Photoexcited Palladium Catalysis.Journal of the American Chemical Society · 2025Article
- Palladium-Catalyzed Gem-Diborylalkylation of Silyl Enol Ethers and N-Vinylacetamide via Diboryl Carbon-Centered Radicals.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Modular synthesis of PAHs from aryl halides and terminal alkynes via photoinduced palladium catalysis.Nature communications · 2025Article
- Cross-dehydrogenative coupling via C(spScience advances · 2025Article
- Excited-State Palladium-Catalyzed Radical Allylic Alkylation: Rapid Access to C2-Allyl Carbohydrates.ACS catalysis · 2025Article
- Illuminating Palladium Catalysis.Accounts of chemical research · 2025Article
- Catalytic Reductive Homocoupling of Benzyl Chlorides Enabled by Zirconocene and Photoredox Catalysis.Precision chemistry · 2025Article
- Bismuth-photocatalysed Heck-type coupling with alkyl and aryl electrophiles.Nature catalysis · 2025Article
- Bifunctional iron-catalyzed alkyne Z-selective hydroalkylation and tandem Z-E inversion via radical molding and flipping.Nature communications · 2024Article
- Radical Replacement Process for Ligated Boryl Radical-Mediated Activation of Unactivated Alkyl Chlorides for C(spJournal of the American Chemical Society · 2024Article
- Recent Advances in Visible Light Induced Palladium Catalysis.Angewandte Chemie (International ed. in English) · 2024Review
- Merging of Light/Dark Palladium Catalytic Cycles Enables Multicomponent Tandem Alkyl Heck/Tsuji-Trost Homologative Amination Reaction toward Allylic Amines.Journal of the American Chemical Society · 2023Article
- Synthesis of palladium nanoparticles stabilized on Schiff base-modified ZnO particles as a nanoscale catalyst for the phosphine-free Heck coupling reaction and 4-nitrophenol reduction.Scientific reports · 2023Article
- Supramolecular Pd@methioine-EDTA-chitosan nanocomposite: an effective and recyclable bio-based and eco-friendly catalyst for the green Heck cross-coupling reaction under mild conditions.Nanoscale advances · 2023Article
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Authors and funding
3 authors.
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Abstract
The use of alkyl chlorides in Pd-catalyzed Mizoroki-Heck coupling reactions remains an unsolved problem despite their significant potential for synthetic utility and applicability. The combination of the high thermodynamic barrier of alkyl chloride activation and kinetic propensity of alkylpalladium complexes to undergo undesired β-hydride elimination provides significant challenges. Herein, a variety of alkyl chlorides, even tertiary chlorides, are shown to efficiently participate in Mizoroki-Heck cross-coupling reactions with excellent functional group compatibility under mild reaction conditions via photoinduced Pd catalysis. The reaction is applied to late-stage functionalizations of diverse biologically significant scaffolds and iterative double Mizoroki-Heck annulations, affording high molecular complexity in a single step. Notably, studies on the kinetic isotope effects in combination with density functional theory (DFT)-computations completely exclude the involvement of a previously proposed β-hydride elimination in the catalytic cycle, revealing that the chlorine atom transfer process is the key catalytic turnover step. This distinctive single-electron transfer mediated reaction pathway resolves a longstanding challenge in traditional two-electron based Pd-catalyzed Mizoroki-Heck cross-coupling with alkyl electrophiles, wherein the β-hydride elimination is involved in the formation of both the desired product and undesired by-products.
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