ArticleJournal of the American Chemical Society2017
Cyclobutene vs 1,3-Diene Formation in the Gold-Catalyzed Reaction of Alkynes with Alkenes: The Complete Mechanistic Picture.
Article in Journal of the American Chemical Society, 2017. 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.
- Gold(I)-Catalyzed Intermolecular Reactions of Alkynes with Carbon Nucleophiles: What We Knowand What We Don't.ACS catalysis · 2026Review
- π-Bonding of Group 11 Metals to a Tantalum Alkylidyne Alkyl Complex Promotes Unusual Tautomerism to Bis-alkylidene and COJournal of the American Chemical Society · 2024Article
- Gold(I)-Catalyzed Intermolecular Formal [4+2] Cycloaddition of O-Aryl Ynol Ethers and Enol Ethers: Synthesis of Chromene Derivatives.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- New-Generation Ligand Design for the Gold-Catalyzed Asymmetric Activation of Alkynes.ChemPlusChem · 2021Review
- Gold-Catalyzed Synthesis of Small Rings.Chemical reviews · 2021Article
- Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step.Angewandte Chemie (International ed. in English) · 2020Article
- MonoauratedChemical science · 2019Article
- Enantioselective Rhodium-Catalyzed Cycloisomerization of 1,6-Allenynes to access 5/6-Fused Bicycle[4.3.0]nonadienes.Nature communications · 2019Article
- Insights into Ag(i)-catalyzed addition reactions of amino alcohols to electron-deficient olefins: competing mechanisms, role of catalyst, and origin of chemoselectivity.RSC advances · 2018Article
- Au-Catalyzed Intermolecular [2+2] Cycloadditions between Chloroalkynes and Unactivated Alkenes.Journal of the American Chemical Society · 2018Article
- Role of σ,π-Digold(I) Alkyne Complexes in Reactions of Enynes.Organometallics · 2018Article
- Enantioselective Synthesis of Cyclobutenes by Intermolecular [2+2] Cycloaddition with Non-CJournal of the American Chemical Society · 2017Article
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Authors and funding
7 authors.
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Abstract
The intermolecular gold(I)-catalyzed reaction between arylalkynes and alkenes leads to cyclobutenes by a [2 + 2] cycloaddition, which takes place stepwise, first by formation of cyclopropyl gold(I) carbenes, followed by a ring expansion. However, 1,3-butadienes are also formed in the case of ortho-substituted arylalkynes by a metathesis-type process. The corresponding reaction of alkenes with aryl-1,3-butadiynes, ethynylogous to arylalkynes, leads exclusively to cyclobutenes. A comprehensive mechanism for the gold(I)-catalyzed reaction of alkynes with alkenes is proposed on the basis of density functional theory calculations, which shows that the two pathways leading to cyclobutenes or dienes are very close in energy. The key intermediates are cyclopropyl gold(I) carbenes, which have been independently generated by retro-Buchner reaction from stereodefined 1a,7b-dihydro-1H-cyclopropa[a]naphthalenes.
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