ArticleJournal of the American Chemical Society2016
Reactions of HDDA-Derived Benzynes with Sulfides: Mechanism, Modes, and Three-Component Reactions.
Article in Journal of the American Chemical Society, 2016. 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.
- 1The Journal of organic chemistry · 2026Article
- Generation of Quaternary Carbons in Cycloalkanones and Lactones with Arynes through a Domino Process.The Journal of organic chemistry · 2024Article
- An Untethered and Formal Intermolecular Hexadehydro-Diels-Alder Reaction: Alkynylboronates with 2-(1,3-Butadiynyl)pyridines.Journal of the American Chemical Society · 2024Article
- Benzyne-Promoted, 1,2-Organic letters · 2023Article
- Sulfonium-based precise alkyl transposition reactions.Science advances · 2023Article
- 1,3-Butadiynamides the Ethynylogous Ynamides: Synthesis, Properties and Applications in Heterocyclic Chemistry.Molecules (Basel, Switzerland) · 2023Review
- Empowering boronic acids as hydroxyl synthons for aryne induced three-component coupling reactions.Chemical science · 2023Article
- Development of an Allenyne-Alkyne [4+2] Cycloaddition and its Application to Total Synthesis of Selaginpulvilin A.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Trapping Reactions of Benzynes Initiated by Intramolecular Nucleophilic Addition of a Carbonyl Oxygen to the Electrophilic Aryne.Organic letters · 2022Article
- Reactivity of Vinyl Epoxides/Oxetanes/Cyclopropanes toward Arynes: Access to Functionalized Phenanthrenes.ACS omega · 2021Article
- Article
- Radial hexadehydro-Diels-Alder reactions.Chem · 2021Article
- Arylhydrazine Trapping of Benzynes: Mechanistic Insights and a Route to Azoarenes.Organic letters · 2021Article
- Hexadehydro-Diels-Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes.Chemical reviews · 2021Review
- One-step synthesis of benzo[Chemical science · 2020Article
- Reactions of HDDA Benzynes withEuropean journal of organic chemistry · 2020Article
- The Aza-hexadehydro-Diels-Alder Reaction.Journal of the American Chemical Society · 2019Article
- Sequential cycloaddition and ring expansion reaction of arynes and methylenebenzothiopheneones: synthesis of a benzo-fused eight-membered ringRSC advances · 2019Article
- Reactions of thermally generated benzynes with six-memberedChemical science · 2019Article
- Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.Chemical reviews · 2019Article
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3 authors.
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Abstract
We report here reactions of alkyl sulfides with benzynes thermally generated by the hexadehydro-Diels-Alder (HDDA) cycloisomerization. The initially produced 1,3-betaine (o-sulfonium/aryl carbanion) undergoes intramolecular proton transfer to generate a more stable S-aryl sulfur ylide. This can react in various manners, including engaging weak acids (HA) in the reaction medium. This can produce transient ion pairs ArSR2(+)A(-) that proceed to the products ArSR + RA. When cyclic sulfides are used, A(-) opens the ring and is incorporated into the product, an outcome that constitutes a versatile, three-component coupling process.
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