ArticleAngewandte Chemie (International ed. in English)2023
Transition-Metal-Free Difunctionalization of Sulfur Nucleophiles.
Article in Angewandte Chemie (International ed. in English), 2023. 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.
- C─S Bond Formation of Aryl Germanes.Angewandte Chemie (International ed. in English) · 2026Article
- SJACS Au · 2026Article
- Thiol-Free Sulfenylation Redefined: A Single-Atom Transfer Pathway to Symmetrical Di(hetero)arylthioethers via B(CJournal of the American Chemical Society · 2026Article
- Once Upon a Time Without DMF: Greener Paths in Peptide and Organic Synthesis.Molecules (Basel, Switzerland) · 2026Review
- Iodoarene Activation: Take a Leap Forward toward Green and Sustainable Transformations.Chemical reviews · 2025Review
- Transition-Metal-FreeJACS Au · 2024Article
- Article
- Syntheses, reactivity, and biological applications of coumarins.Frontiers in chemistry · 2024Review
- Synthesis of Functionalized Pyrrolidinone Scaffolds via Smiles-Truce Cascade.Organic letters · 2023Article
- Synthetic exploration of electrophilic xanthylationChemical science · 2023Article
- DBDMH-Promoted Methylthiolation in DMSO: A Metal-Free Protocol to Methyl Sulfur Compounds with Multifunctional Groups.Molecules (Basel, Switzerland) · 2023Article
- Transition-Metal-Free Difunctionalization of Sulfur Nucleophiles.Angewandte Chemie (International ed. in English) · 2023Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
Efficient protocols for accessing iodo-substituted diaryl and aryl(vinyl) sulfides have been developed using iodonium salts as reactive electrophilic arylation and vinylation reagents. The reactions take place under transition-metal-free conditions, employing odorless and convenient sulfur reagents. A wide variety of functional groups are tolerated in the S-diarylation, enabling the regioselective late-stage application of several heterocycles and drug molecules under mild reaction conditions. A novel S-difunctionalization pathway was discovered using vinyliodonium salts, which proceeds under additive-free reaction conditions and grants excellent stereoselectivity in the synthesis of aryl(vinyl) sulfides. A one-pot strategy combining transition-metal-free diarylation and subsequent reduction provided facile access to electron-rich thioanilines and a direct synthesis of a potential drug candidate derivative. The retained iodo group allows a wide array of further synthetic transformations. Mechanistic insights were elucidated by isolating the key intermediate, and the relevant energy profile was substantiated by DFT calculations.
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Registered trials
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