ArticleAngewandte Chemie (International ed. in English)2020
Acyl Migration versus Epoxidation in Gold Catalysis: Facile, Switchable, and Atom-Economic Synthesis of Acylindoles and Quinoline Derivatives.
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 15 papers.
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15 citing papers in PubMed.
- E/Z Isomerization-Enabled Conversion from Dual-Carbon to Single-Carbon Insertion into an Aromatic System.JACS Au · 2026Article
- Unconventional Ring Opening Triggers Intramolecular C-H Amination of Anthranils via Electrocyclization under Cobalt Catalysis.JACS Au · 2025Article
- Allylic Hydrogen Acidity of 1-Butene Derivatives Coordinated to Transition Metals─A Mechanistic Insight Including Carbonyl-Olefin Metathesis.Inorganic chemistry · 2025Article
- Cobalt phthalocyanine (CoPc) anchored on TiNanoscale advances · 2024Article
- Gold-Catalyzed Cyclization of Yndiamides with Isoxazoles via α-Imino Gold Fischer Carbenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Experimental and Theoretical Investigation of Ion Pairing in Gold(III) Catalysts.Organometallics · 2023Article
- 1,3-Butadiynamides the Ethynylogous Ynamides: Synthesis, Properties and Applications in Heterocyclic Chemistry.Molecules (Basel, Switzerland) · 2023Review
- Gold-Catalyzed Synthesis of Small Rings.Chemical reviews · 2021Article
- Unusual Oxidative Dimerization in the 3-Aminothieno[2,3-ACS omega · 2021Article
- Monitoring of the Pre-Equilibrium Step in the Alkyne Hydration Reaction Catalyzed by Au(III) Complexes: A Computational Study Based on Experimental Evidences.Molecules (Basel, Switzerland) · 2021Article
- Synthesis of Carbazoles and Related Heterocycles from Sulfilimines by Intramolecular C-H Aminations.Angewandte Chemie (International ed. in English) · 2020Article
- Dibenzothiophenesulfilimines: A Convenient Approach to Intermolecular Rhodium-Catalysed C-H Amidation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Gold(I)-Catalyzed Cycloisomerization of 3-Alkoxyl-1,6-diynes: A Facile Access to Bicyclo[2.2.1]hept-5-en-2-ones.Angewandte Chemie (International ed. in English) · 2020Article
- α-Imino Gold Carbene Intermediates from Readily Accessible Sulfilimines: Intermolecular Access to Structural Diversity.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Acyl Migration versus Epoxidation in Gold Catalysis: Facile, Switchable, and Atom-Economic Synthesis of Acylindoles and Quinoline Derivatives.Angewandte Chemie (International ed. in English) · 2020Article
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Abstract
We report a switchable synthesis of acylindoles and quinoline derivatives via gold-catalyzed annulations of anthranils and ynamides. α-Imino gold carbenes, generated in situ from anthranils and an N,O-coordinated gold(III) catalyst, undergo electrophilic attack to the aryl π-bond, followed by unexpected and highly selective 1,4- or 1,3-acyl migrations to form 6-acylindoles or 5-acylindoles. With the (2-biphenyl)di-tert-butylphosphine (JohnPhos) ligand, gold(I) carbenes experienced carbene/carbonyl additions to deliver quinoline oxides. Some of these epoxides are valuable substrates for the preparation of 3-hydroxylquinolines, quinolin-3(4H)-ones, and polycyclic compounds via facile in situ rearrangements. The reaction can be efficiently conducted on a gram scale and the obtained products are valuable substrates for preparing other potentially useful compounds. A computational study explained the unexpected selectivities and the dependency of the reaction pathway on the oxidation state and ligands of gold. With gold(III) the barrier for the formation of the strained oxirane ring is too high; whereas with gold(I) this transition state becomes accessible. Furthermore, energetic barriers to migration of the substituents on the intermediate sigma-complexes support the observed substitution pattern in the final product.
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