In this paper, we develop a method for Friedel-Crafts acylation using metal triflate in deep eutectic solvents. Various metal triflates were tested and provided good to excellent yields of corresponding ketone products. The density functional theory calculation revealed the metal effects on the formation of active intermediate acylium triflate as well as the acidic condition. The metal triflate in the deep eutectic solvent can be recovered and reused with a little loss in the catalytic activity.
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http://dx.doi.org/10.1021/acsomega.2c03944 | DOI Listing |
J Colloid Interface Sci
December 2024
Department of Mechanical Engineering, University of Alberta, 9211-116 Street NW., Edmonton, Alberta T6G 1H9, Canada. Electronic address:
Copper hexacyanoferrate (CuHCF) demonstrates high working voltage, convenient synthesis methods, and economic benefits. However, capacity decay of CuHCF//Zn full cells is usually observed in aqueous electrolytes due to the dissolution of Cu and Fe, as indicated by the irreversible insertion of Zn ions and the consequent formation of ZnCuHCF. To address these challenges, a cathode-oriented electrolyte engineering design employing a methyl acetate (MA) co-solvent with zinc triflate (Zn(OTf)) salt electrolyte is implemented.
View Article and Find Full Text PDFChem Commun (Camb)
December 2024
Department of Chemistry, School of Pharmacy, Air Force Medical University, Xi'an, 710032, China.
An efficient synthesis of continuously substituted quinoline derivatives palladium-catalyzed intramolecular 6- imidoylative cyclization of -alkenyl aryl isocyanides with (hetero)aryl halides or vinylic triflates has been developed. The reaction proceeds through the concerted metalation-deprotonation (CMD) mechanism by activation of a vinyl C-H bond with imidoylpalladium assisted by the carboxylate.
View Article and Find Full Text PDFOrg Lett
December 2024
Department of Chemistry, Indian Institute of Technology, Kharagpur, West Bengal 721302, India.
Development of metal-free conversion of naturally abundant phenols and anilines to the corresponding olefins remains a formidable challenge. The current state of the art relies on the TM-catalyzed Heck coupling of activated phenols (triflates, tosylates, and more) with the olefins. While these advancements are promising, the reaction suffers from branch vs linear selectivity and requires an expensive TM-ligand combination, hazardous organotin reagents, and very high reaction temperature.
View Article and Find Full Text PDFJ Org Chem
December 2024
Department of Chemistry, Sidho-Kanho-Birsha University, Purulia 723104, W.B., India.
Distinctive, green, innovative, and well-organized photoinduced (metal- or photocatalyst-free) regioselective decarbonylative and decarboxylative C-O bond functionalization protocols to access aryl 2-aminobenzoates and 2-substituted benzoxazinone derivatives in excellent yields have been devised. These are achieved through the chemoselective scission of isatoic anhydride with ketones, diaryliodonium triflate, nitroalkene, phthalazinone, and phenol derivatives, which, in turn, served as the representative "electrophilic and nucleophilic" coupling partners. Control experiments and DFT calculations reveal that electrophilic radical-bearing coupling partners specifically follow the decarbonylation pathway, while nucleophilic radical-bearing conjugates facilitate the decarboxylation process.
View Article and Find Full Text PDFInorg Chem
December 2024
Department of Chemistry, University of Colorado Boulder, Boulder, Colorado 80309, United States.
Mono-β-diketonate compounds have been fleetingly observed in base metal catalyzed reactions, which are of current interest as alternatives to precious metal catalyzed reactions. Their isolation has been challenging due to synthetic and structural limitations of acac-type ligands, leading to the development of a related NacNac ligand platform. Herein we report the synthesis of a β-diketone capable of kinetically stabilizing relevant catalytic intermediates.
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