ArticleAngewandte Chemie (International ed. in English)2020
Gold(I)-Catalyzed Haloalkynylation of Aryl Alkynes: Two Pathways, One Goal.
Article in Angewandte Chemie (International ed. in English), 2020. 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.
- Cobalt-Catalyzed Halogen-Retentive C-H Activation and Its Application in Medicinal Chemistry.JACS Au · 2026Article
- Bromide-Mediated Low-Energy RuAngewandte Chemie (International ed. in English) · 2026Article
- Gold(I)-Catalyzed Intermolecular Reactions of Alkynes with Carbon Nucleophiles: What We Knowand What We Don't.ACS catalysis · 2026Review
- Enantioselective cyclization of bromoenynes: mechanistic understanding of gold(i)-catalyzed alkoxycyclizations.Chemical science · 2026Article
- Conformational Effects in Intramolecular C(spOrganic letters · 2025Article
- Approach to Heterospirocycles for Medicinal Chemistry.Organic letters · 2025Article
- Straightforward Synthesis of α-Chloromethylketimines Catalyzed by Gold(I). A Clean Way to Building Blocks.The Journal of organic chemistry · 2022Article
- Selectivity, Speciation, and Substrate Control in the Gold-Catalyzed Coupling of Indoles and Alkynes.Organometallics · 2022Article
- Metal-Catalyzed Haloalkynylation Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
- Ruthenium-CatalyzedJournal of the American Chemical Society · 2020Article
- Cyclopropenylmethyl Cation: A Concealed Intermediate in Gold(I)-Catalyzed Reactions.Angewandte Chemie (International ed. in English) · 2020Article
- Gold(I)-Catalyzed Haloalkynylation of Aryl Alkynes: Two Pathways, One Goal.Angewandte Chemie (International ed. in English) · 2020Article
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2 authors.
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Abstract
Haloalkynylation reactions provide an efficient method for the simultaneous introduction of a halogen atom and an acetylenic unit. For the first time, we report a gold(I)-catalyzed haloalkynylation of aryl alkynes that delivers exclusively the cis addition product. This method enables the simple synthesis of conjugated and halogenated enynes in yields of up to 90 %. Notably, quantum chemical calculations reveal an exceptional interplay between the place of the attack at the chloroacetylene: No matter which C-C bond is formed, the same enyne product is always formed. This is only possible through rearrangement of the corresponding skeleton. Hereby, one reaction pathway proceeds via a chloronium ion with a subsequent aryl shift; in the second case the corresponding vinyl cation is stabilized by a 1,3-chlorine shift.
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