ArticleChemical science2019
Catalytic Au(i)/Au(iii) arylation with the hemilabile MeDalphos ligand: unusual selectivity for electron-rich iodoarenes and efficient application to indoles.
Article in Chemical science, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.
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Who cites it
27 citing papers in PubMed.
- Oxidant-free Au(I)/Au(III) catalysis: Rational development of hemilabile proximity-guided N-heterocyclic carbenes.Science advances · 2026Article
- TheBeilstein journal of organic chemistry · 2026Article
- StereoselectiveACS organic & inorganic Au · 2025Article
- Synthesis of (P^N^C)Gold(III) Complexes via Tandem Oxidative Addition/C-H Auration.ACS organic & inorganic Au · 2025Article
- An Electrochemical Study of Key Catalytically Active Gold Complexes.Angewandte Chemie (International ed. in English) · 2025Article
- Nucleophilic Addition versus Migratory Insertion Pathways in the Gold-Catalyzed Heck Reaction: A Computational Study.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Photosensitized Reductive Elimination of Gold(III) to Enable Esterification of Aryl Iodides with Carboxylic Acids.JACS Au · 2024Article
- (P^N^C) Ligands to Stabilize Gold(III): A Straightforward Access to Hydroxo, Formate, and Hydride Complexes.Inorganic chemistry · 2024Article
- Accessing gold p-acid reactivity under electrochemical anode oxidation (EAO) through oxidation relay.Nature communications · 2023Article
- Gold-catalyzed alkenylation and arylation of phosphorothioates.Chemical science · 2023Article
- Accessing Gold π-Acid Reactivity under Electrochemical Anode Oxidation (EAO) through Oxidation Relay.Research square · 2023Article
- A Hemilabile NHC-Gold Complex and its Application to the Redox Neutral 1,2-Oxyarylation of Feedstock Alkenes.Angewandte Chemie (International ed. in English) · 2023Article
- Copper-catalyzed [1,3]-nitrogen rearrangement ofChemical science · 2023Article
- L-Shaped Heterobidentate Imidazo[1,5-a]pyridin-3-ylidene (N,C)-Ligands for Oxidant-Free AuAngewandte Chemie (International ed. in English) · 2023Article
- Migratory Insertion of CO into a Au-C Bond.Journal of the American Chemical Society · 2022Article
- Mechanistic Insights about the Ligand-Enabled Oxy-arylation/vinylation of Alkenes via Au(I)/Au(III) Catalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Ligand-enabled oxidation of gold(i) complexes withChemical science · 2022Article
- OrganometallicBioconjugate chemistry · 2022Article
- Hemilabile MIC^N ligands allow oxidant-free Au(i)/Au(iii) arylation-lactonization of γ-alkenoic acids.Chemical science · 2022Article
- Gold (I/III)-Catalyzed Trifluoromethylthiolation and Trifluoromethylselenolation of Organohalides.Angewandte Chemie (International ed. in English) · 2022Article
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Abstract
The ability of the hemilabile (P,N) MeDalphos ligand to trigger oxidative addition of iodoarenes to gold has been thoroughly studied. Competition experiments and Hammett correlations substantiate a clear preference of gold for electron-enriched substrates both in stoichiometric oxidative addition reactions and in catalytic C-C cross-coupling with 1,3,5-trimethoxybenzene. This feature markedly contrasts with the higher reactivity of electron-deprived substrates typically encountered with palladium. Based on DFT calculations and detailed analysis of the key transition states (using NBO, CDA and ETS-NOCV methods in particular), the different behavior of the two metals is proposed to result from inverse electron flow between the substrate and metal. Indeed, oxidative addition of iodobenzene is associated with a charge transfer from the substrate to the metal at the transition state for gold, but opposite for palladium. The higher electrophilicity of the gold center favors electron-rich substrates while important back-donation from palladium favors electron-poor substrates. Facile oxidative addition of iodoarenes combined with the propensity of gold(iii) complexes to readily react with electron-rich (hetero)arenes prompted us to apply the (MeDalphos)AuCl complex in the catalytic arylation of indoles, a challenging but very important transformation. The gold complex proved to be very efficient, general and robust. It displays complete regioselectivity for C3 arylation, it tolerates a variety of functional groups at both the iodoarene and indole partners (NO
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