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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2024-12-01
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| Online Access: | https://www.mdpi.com/1420-3049/29/23/5756 |
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| author | Sara Colombo Julie Oble Giovanni Poli Leonardo Lo Presti Giovanni Macetti Alessandro Contini Gianluigi Broggini Marta Papis Camilla Loro |
| author_facet | Sara Colombo Julie Oble Giovanni Poli Leonardo Lo Presti Giovanni Macetti Alessandro Contini Gianluigi Broggini Marta Papis Camilla Loro |
| author_sort | Sara Colombo |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-94047080aa2349f181d09fbb6490693d |
| institution | DOAJ |
| issn | 1420-3049 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj-art-94047080aa2349f181d09fbb6490693d2025-08-20T02:50:40ZengMDPI AGMolecules1420-30492024-12-012923575610.3390/molecules29235756Doubly Metathetic NiCl<sub>2</sub>-Catalyzed Coupling Between Bis(2-oxazolines) and Aldehydes: A Novel Access to Bis(ester-imine) DerivativesSara Colombo0Julie Oble1Giovanni Poli2Leonardo Lo Presti3Giovanni Macetti4Alessandro Contini5Gianluigi Broggini6Marta Papis7Camilla Loro8Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell’Insubria, Via Valleggio 9, 22100 Como, ItalyIPCM, Institut Parisien de Chimie Moléculaire, CNRS, Faculté des Sciences et Ingénierie, Sorbonne Université, 4 Place Jussieu, 75005 Paris, FranceIPCM, Institut Parisien de Chimie Moléculaire, CNRS, Faculté des Sciences et Ingénierie, Sorbonne Université, 4 Place Jussieu, 75005 Paris, FranceDipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, 20133 Milano, ItalyDipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, 20133 Milano, ItalyDipartimento di Scienze Farmaceutiche, DISFARM, Università degli Studi di Milano, Via Venezian 21, 20133 Milano, ItalyDipartimento di Scienza e Alta Tecnologia, Università degli Studi dell’Insubria, Via Valleggio 9, 22100 Como, ItalyDipartimento di Scienza e Alta Tecnologia, Università degli Studi dell’Insubria, Via Valleggio 9, 22100 Como, ItalyDipartimento di Scienza e Alta Tecnologia, Università degli Studi dell’Insubria, Via Valleggio 9, 22100 Como, ItalyThe 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.https://www.mdpi.com/1420-3049/29/23/5756nickel catalysisbis(2-oxazolines)aldehydesLewis acidsmalonic estersimines |
| spellingShingle | Sara Colombo Julie Oble Giovanni Poli Leonardo Lo Presti Giovanni Macetti Alessandro Contini Gianluigi Broggini Marta Papis Camilla Loro Doubly Metathetic NiCl<sub>2</sub>-Catalyzed Coupling Between Bis(2-oxazolines) and Aldehydes: A Novel Access to Bis(ester-imine) Derivatives Molecules nickel catalysis bis(2-oxazolines) aldehydes Lewis acids malonic esters imines |
| title | Doubly Metathetic NiCl<sub>2</sub>-Catalyzed Coupling Between Bis(2-oxazolines) and Aldehydes: A Novel Access to Bis(ester-imine) Derivatives |
| title_full | Doubly Metathetic NiCl<sub>2</sub>-Catalyzed Coupling Between Bis(2-oxazolines) and Aldehydes: A Novel Access to Bis(ester-imine) Derivatives |
| title_fullStr | Doubly Metathetic NiCl<sub>2</sub>-Catalyzed Coupling Between Bis(2-oxazolines) and Aldehydes: A Novel Access to Bis(ester-imine) Derivatives |
| title_full_unstemmed | Doubly Metathetic NiCl<sub>2</sub>-Catalyzed Coupling Between Bis(2-oxazolines) and Aldehydes: A Novel Access to Bis(ester-imine) Derivatives |
| title_short | Doubly Metathetic NiCl<sub>2</sub>-Catalyzed Coupling Between Bis(2-oxazolines) and Aldehydes: A Novel Access to Bis(ester-imine) Derivatives |
| title_sort | doubly metathetic nicl sub 2 sub catalyzed coupling between bis 2 oxazolines and aldehydes a novel access to bis ester imine derivatives |
| topic | nickel catalysis bis(2-oxazolines) aldehydes Lewis acids malonic esters imines |
| url | https://www.mdpi.com/1420-3049/29/23/5756 |
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