ArticleAdvanced synthesis & catalysis2022
Dimsyl Anion Enables Visible-Light-Promoted Charge Transfer in Cross-Coupling Reactions of Aryl Halides.
Article in Advanced synthesis & catalysis, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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16 citing papers in PubMed, 48 citations in OpenAlex.
- Deprotection of benzyl ethersGreen chemistry : an international journal and green chemistry resource : GC · 2026Article
- Achieving Diverse Functionalizations of Electron-Deficient Aryl Halides via Carbonate-Mediated Electron-Donor-Acceptor Complexes.European journal of organic chemistry · 2026Article
- Generation of a Ground-State Electron Donor Utilizing Stored Light Energy.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- PotassiumACS omega · 2026Article
- EDA Complex-Mediated C(spEuropean journal of organic chemistry · 2026Article
- Dramatic expansion of bimodal redox window of indigo by two-electron redox processes.Nature communications · 2025Article
- EDA Complex-Driven Desaturation of Heterocyclic Carbonyl Compounds Enabled by HFIP.Angewandte Chemie (International ed. in English) · 2025Article
- Sequential EDA/HAT Enables C(spOrganic letters · 2025Article
- Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations.Chemical reviews · 2025Review
- Article
- Light-assisted functionalization of aryl radicals towards metal-free cross-coupling.Nature reviews. Chemistry · 2025Review
- Solvent Anions Enable Photoinduced Borylation and Phosphonation of Aryl Halides via EDA Complexes.Organic letters · 2022Article
- Photoinduced C(spOrganic letters · 2022Article
- Photoredox Polyfluoroarylation of Alkyl Halides via Halogen Atom Transfer.Organic letters · 2022Article
- Transition-Metal-Free Photoredox Phosphonation of Aryl C-N and C-X Bonds in Aqueous Solvent Mixtures.ACS sustainable chemistry & engineering · 2022Article
- Metal-free visible-light-promoted C(spGreen chemistry : an international journal and green chemistry resource : GC · 2021Article
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Authors and funding
4 authors at 1 institution in 1 country.
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Abstract
A methodology is reported for visible-light-promoted synthesis of unsymmetrical chalcogenides enabled by dimsyl anion in the absence of transition-metals or photoredox catalysts. The cross-coupling reaction between aryl halides and diaryl dichalcogenides proceeds with electron-rich, electron-poor, and heteroaromatic moieties. Mechanistic investigations using UV-Vis spectroscopy, time-dependent density functional theory (TD-DFT) calculations, and control reactions suggest that dimsyl anion forms an electron-donor-acceptor (EDA) complex capable of absorbing blue light, leading to a charge transfer responsible for generation of aryl radicals from aryl halides. This previously unreported mechanistic pathway may be applied to other light-induced transformations performed in DMSO in the presence of bases and aryl halides.
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