Εξειδίκευση τύπου :	Άρθρο σε επιστημονικό περιοδικό
Τίτλος:	An Efficient Light-Mediated Protocol for the Direct Amide Bond Formation via a Novel Carboxylic Acid Photoactivation Mode by Pyridine-CBr4
Δημιουργός/Συγγραφέας:	Mountanea, Olga G Psathopoulou, Danai Mantzourani, Christiana Kokotou, Maroula G Routsi, E Alexandros [EL] Τζέλη, Δήμητρα[EN] Tzeli, Demeter Kokotos, Christoforos G Kokotos, George
Ημερομηνία:	2023-06-22
Γλώσσα:	Αγγλικά
ISSN:	0947-6539 1521-3765
DOI:	10.1002/chem.202300556
Άλλο:	37015030
Περίληψη:	The direct amide bond formation between a carboxylic acid and an amine still constitutes a challenging reaction for both academia and industry. We demonstrate herein that several pairs of amines (halogen bond acceptors) and organohalogen sources may be used for the photochemical amidation reaction under either UVA or sunlight irradiation. Our studies led to the identification of pyridine-CBr4 as an efficient agent to perform amide synthesis under LED 370 nm irradiation, avoiding super-stoichiometric quantities. An extended substrate scope was demonstrated, showing that the widely used amino and carboxyl protecting groups are compatible with this photochemical protocol, while a number of industrially interesting products and bioactive compounds were synthesized. Direct infusion-high resolution mass spectrometry studies suggest an unprecedented type of carboxylic acid activation mode upon irradiation, involving the generation of a symmetric anhydride, an active ester with pyridine N-oxide and a mixed anhydride with hypobromous acid.
Τίτλος πηγής δημοσίευσης:	Chemistry (Weinheim an der Bergstrasse, Germany)
Τόμος/Κεφάλαιο:	29
Τεύχος:	35
Θεματική Κατηγορία:	[EL] Χημική μηχανική[EN] Chemical engineering [EL] Χημεία[EN] Chemistry
Λέξεις-Κλειδιά:	DFT calculations Amide bond formation Halogen bonding Light-mediated chemistry Peptides
Κάτοχος πνευματικών δικαιωμάτων:	© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Ηλεκτρονική διεύθυνση στον εκδότη (link):	https://doi.org/10.1002/chem.202300556
Σημειώσεις:	The research presented was carried out within the framework of a Stavros Niarchos Foundation grant to the National and Kapodistrian University of Athens (G.K.). The authors gratefully acknowledge the Hellenic Foundation for Research and Innovation (H.F.R.I.), since this research project was supported by the Hellenic Foundation for Research and Innovation (H.F.R.I.) under the “1st Call for H.F.R.I. Research Projects to support Faculty Members & Researchers and the Procurement of High-cost research equipment grant” (grant number 655) (C.G.K.). The research work was supported by the Hellenic Foundation for Research and Innovation (H.F.R.I.) under the H.F.R.I. PhD Fellowship grant (Fellowship Number: 1338) (O.G.M.).
Εμφανίζεται στις συλλογές:	Ινστιτούτο Θεωρητικής και Φυσικής Χημείας (ΙΘΦΧ) - Επιστημονικό έργο