The coupling between bis(2-oxazolines) and two equivalents of aromatic aldehydes in the presence of catalytic amounts of NiCl2 affords an ester-imine product in synthetically useful yields. This virtually unknown, 100% atom-economic transformation involves the formal metathesis between the C=N double bond of the bis(2-oxazoline) moiety, which undergoes ring-opening, and the C=O double bond of the aldehyde. The scope of this transformation is studied, and a mechanism is proposed based on DFT calculations.
Doubly Metathetic NiCl2-Catalyzed Coupling Between Bis(2-oxazolines) and Aldehydes: A Novel Access to Bis(ester-imine) Derivatives / C. Sara, J. Oble, G. Poli, L. LO PRESTI, G. Macetti, A. Contini, G. Broggini, M. Papis, C. Loro. - In: MOLECULES. - ISSN 1420-3049. - 29:23(2024 Dec 05), pp. 5756.1-5756.15. [10.3390/molecules29235756]
Doubly Metathetic NiCl2-Catalyzed Coupling Between Bis(2-oxazolines) and Aldehydes: A Novel Access to Bis(ester-imine) Derivatives
L. LO PRESTI;G. Macetti;A. Contini;
2024
Abstract
The coupling between bis(2-oxazolines) and two equivalents of aromatic aldehydes in the presence of catalytic amounts of NiCl2 affords an ester-imine product in synthetically useful yields. This virtually unknown, 100% atom-economic transformation involves the formal metathesis between the C=N double bond of the bis(2-oxazoline) moiety, which undergoes ring-opening, and the C=O double bond of the aldehyde. The scope of this transformation is studied, and a mechanism is proposed based on DFT calculations.
| File | Dimensione | Formato | |
|---|---|---|---|
|
molecules-29-05756.pdf
accesso aperto
Tipologia:
Publisher's version/PDF
Dimensione
2.36 MB
Formato
Adobe PDF
|
2.36 MB | Adobe PDF | Visualizza/Apri |
Pubblicazioni consigliate
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
