ArticleNature communications2020
Transition-metal-free formal cross-coupling of aryl methyl sulfoxides and alcohols via nucleophilic activation of C-S bond.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
What it found
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Who cites it
8 citing papers in PubMed.
- Deprotonation-controlled copper-free Pd-catalyzed Sonogashira couplingRSC advances · 2026Article
- An Iron-Catalyzed Sustainable Functional Group Transfer Strategy for In-Water Transformation of Organic Sulfides to Sulfoxides by a Hydroxylamine-Derived Oxidant.ChemSusChem · 2025Article
- Unveiling the Significance of tert-Butoxides in Transition Metal-Free Cross-Coupling Reactions.Topics in current chemistry (Cham) · 2024Review
- Decarboxylative Sulfinylation Enables a Direct, Metal-Free Access to Sulfoxides from Carboxylic Acids.Angewandte Chemie (International ed. in English) · 2022Article
- Synthesis of Polysubstituted Ferrocenesulfoxides.Molecules (Basel, Switzerland) · 2022Article
- Ni-Catalyzed Borylation of Aryl Sulfoxides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Iterative Exponential Growth of Oxygen-Linked Aromatic Polymers Driven by Nucleophilic Aromatic Substitution Reactions.Frontiers in chemistry · 2021Article
- The recent advancement of low-dimensional nanostructured materials for drug delivery and drug sensing application: A brief review.Journal of molecular liquids · 2020Review
Corrections and comments
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Authors and funding
8 authors.
Funding
Abstract
Employment of sulfoxides as electrophiles in cross-coupling reactions remains underexplored. Herein we report a transition-metal-free cross-coupling strategy utilizing aryl(heteroaryl) methyl sulfoxides and alcohols to afford alkyl aryl(heteroaryl) ethers. Two drug molecules were successfully prepared using this protocol as a key step, emphasizing its potential utility in medicinal chemistry. A DFT computational study suggests that the reaction proceeds via initial addition of the alkoxide to the sulfoxide. This adduct facilitates further intramolecular addition of the alkoxide to the aromatic ring wherein charge on the aromatic system is stabilized by the nearby potassium cation. Rate-determining fragmentation then delivers methyl sulfenate and the aryl or heteroaryl ether. This study establishes the feasibility of nucleophilic addition to an appended sulfoxide as a means to form a bond to aryl(heteroaryl) systems and this modality is expected to find use with many other electrophiles and nucleophiles leading to new cross-coupling processes.
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Registered trials
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