Doubly Metathetic NiCl<sub>2</sub>-Catalyzed Coupling Between Bis(2-oxazolines) and Aldehydes: A Novel Access to Bis(ester-imine) Derivatives

Doubly Metathetic NiCl<sub>2</sub>-Catalyzed Coupling Between Bis(2-oxazolines) and Aldehydes: A Novel Access to Bis(ester-imine) Derivatives

The coupling between bis(2-oxazolines) and two equivalents of aromatic aldehydes in the presence of catalytic amounts of NiCl<sub>2</sub> affords an ester-imine product in synthetically useful yields. This virtually unknown, 100% atom-economic transformation involves the formal metathesi...

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Bibliographic Details
Main Authors: Sara Colombo, Julie Oble, Giovanni Poli, Leonardo Lo Presti, Giovanni Macetti, Alessandro Contini, Gianluigi Broggini, Marta Papis, Camilla Loro
Format: Article
Language:English
Published: MDPI AG 2024-12-01
Series:Molecules
Subjects:
nickel catalysis
bis(2-oxazolines)
aldehydes
Lewis acids
malonic esters
imines
Online Access:https://www.mdpi.com/1420-3049/29/23/5756
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Summary:The coupling between bis(2-oxazolines) and two equivalents of aromatic aldehydes in the presence of catalytic amounts of NiCl<sub>2</sub> 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.
ISSN:1420-3049

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