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Phosphine-boranes do not promote oxidative addition of acyl chlorides to gold, but the phosphine-borane gold triflimide complex [PrP(-CH)BCy]AuNTf was found to catalyze the coupling of acyl chlorides and aryl stannanes. The reaction involves aryl/chloride-bridged dinuclear gold(i) complexes as key intermediates, as substantiated by spectroscopic and crystallographic analyses. Similar to Pd(0)/Pd(ii)-catalyzed Stille coupling with phosphine-borane ligands, the gold-catalyzed variant shows complete chemoselectivity for acyl chlorides over aryl iodides and bromides, enabling straightforward access to halogenated aryl ketones.
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http://dx.doi.org/10.1039/d3sc06193k | DOI Listing |
RSC Adv
August 2025
Laboratoire de Développement Chimique, Galénique et Pharmacologique des Médicaments, Faculté de Pharmacie de Monastir, Université de Monastir Rue Avicenne 5000 Monastir Tunisia
The Friedel-Crafts acylation of arenes is a fundamental reaction extensively employed in both academic research and industrial applications. A significant limitation of this reaction is the requirement for stoichiometric amounts of Lewis acid catalysts, which are typically sensitive and generate considerable waste. In this study, we present an improved catalytic approach for the Friedel-Crafts acylation of activated arenes.
View Article and Find Full Text PDFFitoterapia
August 2025
Freie Universität Berlin, Institute of Pharmacy, Königin-Luise-Str. 2+4, 14195 Berlin, Germany. Electronic address:
Long-chain fatty acyl solamines, recently identified in the leaves of Solanum bulbocastanum Dun., have been shown to confer resistance against plant pests such as the Colorado potato beetle and the phytopathogenic oomycete Phytophthora infestans (Mont.) de Bary.
View Article and Find Full Text PDFChem Commun (Camb)
August 2025
College of Chemical Engineering, Zhejiang University of Technology, Chaowang Road 18#, Hangzhou 310014, China.
The nickel-catalyzed hydroacylation of acrylates with carboxylic acids is described herein. The reaction exhibits a broad substrate scope of acyl donors. Aromatic and aliphatic carboxylic acids are amenable to this reaction.
View Article and Find Full Text PDFJ Am Chem Soc
August 2025
Organic Chemistry Department (Módulo 1), Universidad Autónoma de Madrid, C/Francisco Tomas y Valiente 7, 28049 Madrid, Spain.
Acyl azolium salts have been recently described as good HAT mediators in their excited state-similarly to diaryl ketones-and good acylating reagents, with the beneficial property of enabling incorporation of the acyl residue into the final molecule. Nevertheless, despite significant synthetic efforts in the field, knowledge and understanding of the key reactive intermediates─especially through spectroscopic investigations─remain elusive. Herein, we present a photochemical study of the reactivity of acyl azolium salts that comprises the detection and characterization of the triplet excited state and the decisive ketyl radical intermediate.
View Article and Find Full Text PDFJ Org Chem
August 2025
School of Pharmacy, Shandong Second Medical University, Weifang 261053, China.
A practical and efficient protocol for one-pot synthesis of α-ketoamides has been developed through ligand-free copper-mediated using commercially available 2-bromo/chloro-2,2-difluorophenylethanones and primary amines as starting materials. The reaction exhibits moderate to good yields, broad functional group tolerance, and mild reaction conditions. Mechanistic studies indicate a plausible pathway involving copper-mediated oxidative elimination in DMSO to generate a key acyl fluoride intermediate, which subsequently reacts with aniline to afford the corresponding ketoamide.
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