ArticleNature chemistry2018
The domino hexadehydro-Diels-Alder reaction transforms polyynes to benzynes to naphthynes to anthracynes to tetracynes (and beyond?).
Article in Nature chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Linearly acenaphthylene-fused pentacene exhibiting efficient singlet fission.Chemical science · 2026Article
- Sulfonyl-Directed Photoinduced Dehydro-Diels-Alder Reaction of Aryl Maleimides: Enabling Regioselective Naphthalene Synthesis.JACS Au · 2026Article
- PAH Induction upon Pyrolysis of Hydroxyl-Terminated Polybutadiene-Based Solid Rocket Fuels.The journal of physical chemistry. A · 2025Article
- Hexadehydro Diels-Alder/Alkynyliodanation Cascade: A Highly Regioselective Entry to Polycyclic Aromatics.Organic letters · 2025Article
- 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
- Advances in the synthesis of nitrogen-containing heterocyclic compounds byRSC advances · 2023Review
- Divergent synthesis of benzazepines and bridged polycycloalkanones via dearomative rearrangement.Nature communications · 2022Article
- Domino Dehydrative π-Extension: A Facile Path to Extended Perylenes and Terrylenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Radial hexadehydro-Diels-Alder reactions.Chem · 2021Article
- "Kobayashi Benzynes" as Hexadehydro-Diels-Alder Diynophiles.Organic letters · 2021Article
- Diazocarbonyl and Related Compounds in the Synthesis of Azoles.Molecules (Basel, Switzerland) · 2021Review
- Hexadehydro-Diels-Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes.Chemical reviews · 2021Review
- Diels-Alder Cycloaddition to the Bay Region of Perylene and Its Derivatives as an Attractive Strategy for PAH Core Expansion: Theoretical and Practical Aspects.Molecules (Basel, Switzerland) · 2020Review
- Direct observation ofChemical science · 2020Article
- Silyl Tosylate Precursors to Cyclohexyne, 1,2-Cyclohexadiene, and 1,2-Cycloheptadiene.Organic letters · 2020Article
- Consecutive HDDA and TDDA reactions of silicon-tethered tetraynes for the synthesis of dibenzosilole-fused polycyclic compounds and their unique reactivity.Chemical science · 2019Article
- Cyclic Alkyne Approach to Heteroatom-Containing Polycyclic Aromatic Hydrocarbon Scaffolds.Angewandte Chemie (International ed. in English) · 2019Article
- One-Pot, Three-Aryne Cascade Strategy for Naphthalene Formation from 1,3-Diynes and 1,2-Benzdiyne Equivalents.Journal of the American Chemical Society · 2019Article
- CuAngewandte Chemie (International ed. in English) · 2018Article
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2 authors.
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Abstract
Polyacenes are organic compounds that have multiple, fused, aromatic rings. These highly conjugated molecules often have interesting photonic and/or electronic properties that afford them the potential for application in a host of organoelectronic devices such as sensors, light-emitting diodes, photovoltaic devices and field-effect transistors. Here, we show the development and use of the domino hexadehydro-Diels-Alder reaction to synthesize structurally diverse polyacenes from acyclic polyyne precursors. The key event in these transformations is the successive reaction of multiple 1,3-butadiyne units with a series of in-situ-generated, diynophilic arynes. The polyyne substrates were designed to allow for rapid engagement of each progressively larger aryne following the initiating (and ratelimiting) production of the first reactive intermediate-the benzyne. We show that aryne-trapping reactions are broad in scope and that these cascade or domino processes can be quite efficient.
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