Εξειδίκευση τύπου :	Άρθρο σε επιστημονικό περιοδικό
Τίτλος:	Electron Donor-Acceptor Complex-Assisted Photochemical Conversion of O-2-Nitrobenzyl Protected Hydroxamates to Amides
Δημιουργός/Συγγραφέας:	Gerogiannopoulou, Anna-Dimitra D Mountanea, Olga G Routsi, E Alexandros [EL] Τζέλη, Δήμητρα[EN] Tzeli, Demeter Kokotos, Christoforos G Kokotos, George
Ημερομηνία:	2024-12-10
Γλώσσα:	Αγγλικά
ISSN:	0947-6539 1521-3765
DOI:	10.1002/chem.202402984
Άλλο:	39343744
Περίληψη:	The hydroxamic acid functionality is present in various medicinal agents and has attracted special interest for synthetic transformations in both organic and medicinal chemistry. The N-O bond cleavage of hydroxamic acid derivatives provides an interesting transformation for the generation of various products. We demonstrate, herein, that O-benzyl-type protected hydroxamic acids may undergo photochemical N-O bond cleavage, in the presence or absence of a catalyst, leading to amides. Although some O-benzyl protected aromatic hydroxamates may be photochemically converted to amides in the presence of a base and anthracene as the catalyst, employing O-2-nitrobenzyl group allowed the smooth conversion of both aliphatic and aromatic hydroxamates to primary or secondary amides in good to excellent yields in the presence of an amine, bypassing the need of a catalyst. DFT and UV-Vis studies supported the effective generation of an electron donor-acceptor (EDA) complex between O-2-nitrobenzyl hydroxamates and amines, which enabled the successful product formation under these photochemical conditions. An extensive substrate scope was demonstrated, showcasing that both aliphatic and aromatic hydroxamates are compatible with this protocol, affording a wide variety of primary and secondary amides.
Τίτλος πηγής δημοσίευσης:	Chemistry (Weinheim an der Bergstrasse, Germany)
Τόμος/Κεφάλαιο:	30
Τεύχος:	69
Θεματική Κατηγορία:	[EL] Οργανική χημεία[EN] Organic chemistry [EL] Φωτοχημεία[EN] Photochemistry
Λέξεις-Κλειδιά:	DFT calculations electron donor-acceptor complex hydroxamates light-mediated chemistry O-2-Nitrobenzyl
Κάτοχος πνευματικών δικαιωμάτων:	© 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH
Όροι και προϋποθέσεις δικαιωμάτων:	This is an open access article under the terms of the Creative Commons Attribution-NonCommercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
Ηλεκτρονική διεύθυνση στον εκδότη (link):	https://doi.org/10.1002/chem.202402984
Εμφανίζεται στις συλλογές:	Ινστιτούτο Θεωρητικής και Φυσικής Χημείας (ΙΘΦΧ) - Επιστημονικό έργο