ArticleNature chemistry2014
The aromatic ene reaction.
Article in Nature chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed.
- Advances in the synthesis of nitrogen-containing heterocyclic compounds byRSC advances · 2023Review
- Efficient Heterogeneous Copper-Catalyzed Alder-Ene Reaction of Allenynamides to Pyrrolines.ACS catalysis · 2022Article
- Article
- Hexadehydro-Diels-Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes.Chemical reviews · 2021Review
- Room Temperature Ionic Liquids in Asymmetric Hetero-Ene Type Reactions: Improving Organocatalyst Performance at Lower Temperatures.Molecules (Basel, Switzerland) · 2021Article
- Enantiomeric Separation of New Chiral Azole Compounds.Molecules (Basel, Switzerland) · 2021Article
- An enzymatic Alder-ene reaction.Nature · 2020Article
- Reactions of HDDA Benzynes withEuropean journal of organic chemistry · 2020Article
- Reactions of thermally generated benzynes with six-memberedChemical science · 2019Article
- Consecutive HDDA and TDDA reactions of silicon-tethered tetraynes for the synthesis of dibenzosilole-fused polycyclic compounds and their unique reactivity.Chemical science · 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
- 2-Bromo-6-(chlorodiisopropylsilyl)phenyl tosylate as an efficient platform for intramolecular benzyne-diene [4 + 2] cycloaddition.Chemical science · 2019Article
- Alder-ene reactions driven by high steric strain and bond angle distortion to form benzocyclobutenes.Chemical science · 2019Article
- Analyzing Reaction Rates with the Distortion/Interaction-Activation Strain Model.Angewandte Chemie (International ed. in English) · 2017Review
- Photochemical Hexadehydro-Diels-Alder Reaction.Journal of the American Chemical Society · 2017Article
- The Phenol-Ene Reaction: Biaryl Synthesis via Trapping Reactions between HDDA-Generated Benzynes and Phenolics.Organic letters · 2016Article
- Hexadehydro-Diels-Alder (HDDA)-Enabled Carbazolyne Chemistry: Single Step, de Novo Construction of the Pyranocarbazole Core of Alkaloids of the Murraya koenigii (Curry Tree) Family.Journal of the American Chemical Society · 2016Article
- The pentadehydro-Diels-Alder reaction.Nature · 2016Article
- Reactions of HDDA-Derived Benzynes with Sulfides: Mechanism, Modes, and Three-Component Reactions.Journal of the American Chemical Society · 2016Article
- On-surface generation and imaging of arynes by atomic force microscopy.Nature chemistry · 2015Article
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2 authors.
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Abstract
The ene reaction is a pericyclic process in which an alkene with an allylic hydrogen atom (the ene donor) reacts with a second unsaturated species (the enophile) to form a new product with a transposed π-bond. The aromatic ene reaction, in which the alkene component is embedded in an aromatic ring, has only been reported in a few (four) instances and has proceeded in low yield (≤6%). Here, we show efficient aromatic ene reactions in which a thermally generated aryne intermediate engages a pendant m-alkylarene substituent to produce a dearomatized isotoluene, itself another versatile but rare reactive intermediate. Our experiments were guided by computational studies that revealed structural features conducive to the aromatic ene process. We proceeded to identify a cascade comprising three reactions: (1) hexadehydro-Diels-Alder (for aryne generation), (2) intramolecular aromatic ene and (3) bimolecular Alder ene. The power of this cascade is evident from the structural complexity of the final products, the considerable scope, and the overall efficiency of these multistage, reagent- and by-product-free, single-pot transformations.
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