Εξειδίκευση τύπου :	Άρθρο σε επιστημονικό περιοδικό
Τίτλος:	A Ligand-Free Approach towards Coumarin Analogs via Natural Deep Eutectic Solvent-Mediated Suzuki-Miyaura Coupling
Δημιουργός/Συγγραφέας:	Katopodi, Annita Nikolaou, Nikolaos Kakokefalou, Vasiliki Alexandratou, Eleni Matzapetakis, Manolis [EL] Ζερβού, Μαρία[EN] Zervou, Maria Detsi, Anastasia
Ημερομηνία:	2024-09-16
Γλώσσα:	Αγγλικά
ISSN:	1420-3049
DOI:	10.3390/molecules29184398
Άλλο:	39339393
Περίληψη:	A ligand-free approach for the Suzuki-Miyaura cross coupling reaction using Natural Deep Eutectic Solvents (NaDES) towards coumarin analogs is described. A model reaction between the synthetically prepared 3-(4-acetyloxy-phenyl)-6-bromo-4-methyl-coumarin (3b) and phenylboronic acid was performed in five different NaDES as well as in pure glycerol, using two inorganic bases and palladium catalysts. The reaction proceeded smoothly in Choline Chloride/Glycerol (ChCl/Gly) and Betaine/Glycerol (Bet/Gly) NaDES at 90 °C in 24 h, affording the desired product in high yields up to 95%. The combination of K2CO3, Pd(OAc)2 and ChCl/Gly NaDES provided optimum yields and high purity of the desired compounds, while the solvent was successfully recycled and reused up to two times. The developed methodology is applicable to boronic acids bearing various substituents. The formation of palladium nanoparticles in the reaction mixture was observed, and the size of the nanoparticles was associated with the reaction yield. In addition, in all the glycerol-based NaDES, an effective removal of the acetyl group of the acetyloxy-coumarin analogs was observed; thus, it is noteworthy that the Suzuki-Miyaura coupling and the deacetylation reaction were achieved in one pot. The ten novel coumarin derivatives synthesized were structurally characterized using 1D and 2D NMR spectroscopy and were tested for their cytotoxicity against the A431 squamous cancer cell line, presenting significant activity.
Τίτλος πηγής δημοσίευσης:	Molecules (Basel, Switzerland)
Τόμος/Κεφάλαιο:	29
Τεύχος:	18
Θεματική Κατηγορία:	[EL] Φασματοσκοπία[EN] Spectroscopy [EL] Βιοχημεία[EN] Biochemistry [EL] Νανοτεχνολογία[EN] Nanotechnology [EL] Οργανική χημεία[EN] Organic chemistry
Λέξεις-Κλειδιά:	Deep Eutectic Solvents Suzuki–Miyaura reaction coumarins palladium nanoparticles
Κάτοχος πνευματικών δικαιωμάτων:	© 2024 by the authors. Licensee MDPI, Basel, Switzerland.
Όροι και προϋποθέσεις δικαιωμάτων:	This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https:// creativecommons.org/licenses/by/ 4.0/).
Ηλεκτρονική διεύθυνση στον εκδότη (link):	https://doi.org/10.3390/molecules29184398
Εμφανίζεται στις συλλογές:	Ινστιτούτο Χημικής Βιολογίας - Επιστημονικό έργο