ArticleJournal of the American Chemical Society2019
One-Pot, Three-Aryne Cascade Strategy for Naphthalene Formation from 1,3-Diynes and 1,2-Benzdiyne Equivalents.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Hexadehydro Diels-Alder/Alkynyliodanation Cascade: A Highly Regioselective Entry to Polycyclic Aromatics.Organic letters · 2025Article
- Benzyne-Promoted, 1,2-Organic letters · 2023Article
- Advances in the synthesis of nitrogen-containing heterocyclic compounds byRSC advances · 2023Review
- Radial hexadehydro-Diels-Alder reactions.Chem · 2021Article
- Hexadehydro-Diels-Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes.Chemical reviews · 2021Review
- Arynes as Radical Acceptors: TEMPO-Mediated Cascades Comprising Addition, Cyclization, and Trapping.Angewandte Chemie (International ed. in English) · 2021Article
- One-step synthesis of benzo[Chemical science · 2020Article
- Uncovering the Neglected Similarities of Arynes and Donor-Acceptor Cyclopropanes.Angewandte Chemie (International ed. in English) · 2020Review
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
Here we disclose a cascade strategy for naphthyne formation that capitalizes on the traditional benzyne generation (i.e., from an ortho-silyl aryl triflate) and the thermal hexadehydro-Diels-Alder (HDDA) reaction. In this transformation, three distinct aryne species work in tandem, two of which can be formally considered as a 1,2-benzidyne, and each undergoes a different type of trapping event. Many examples were explored by varying the naphthyne capture chemistry as well as the 1,2-benzdiyne equivalent. This strategy enables rapid construction of various naphthalene products and has potential for the synthesis of extended polycyclic arenes.
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Registered trials
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