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Mechanochemical Cu(II) complexes and propargylamine synthetic adventures

Mechanochemical Cu(II) complexes and propargylamine synthetic adventures
Mechanochemical Cu(II) complexes and propargylamine synthetic adventures

We synthesized and characterized known and new Cu(ii)-salen complexes and investigated their efficacy in yielding propargylamines (PAs) via an A3 coupling reaction mechanochemically. Although the method appears simple, we explicitly describe synthetic obstacles that urge unavoidable solvent use to isolate the molecular entities in high purity. The recovered complexes retain structure and catalytic efficacy, and a library of twenty-four known and unknown PAs are isolated in very good to excellent yields. The scope and limitations of this method are presented.

528-535
Al Jomeh, Ghadah Abdullah S.
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McGown, Andrew
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Richards, Emma
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Tizzard, Graham J.
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Coles, Simon J.
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González-Méndez, Ramón
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Dadswell, Chris
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Spencer, John
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Kostakis, George E.
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Al Jomeh, Ghadah Abdullah S.
eb43dfca-cc79-47f7-a396-05127563b50d
McGown, Andrew
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Richards, Emma
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Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
González-Méndez, Ramón
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Dadswell, Chris
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Spencer, John
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Kostakis, George E.
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Al Jomeh, Ghadah Abdullah S., McGown, Andrew, Richards, Emma, Tizzard, Graham J., Coles, Simon J., González-Méndez, Ramón, Dadswell, Chris, Spencer, John and Kostakis, George E. (2024) Mechanochemical Cu(II) complexes and propargylamine synthetic adventures. RSC Sustainability, 2 (2), 528-535. (doi:10.1039/d3su00315a).

Record type: Article

Abstract

We synthesized and characterized known and new Cu(ii)-salen complexes and investigated their efficacy in yielding propargylamines (PAs) via an A3 coupling reaction mechanochemically. Although the method appears simple, we explicitly describe synthetic obstacles that urge unavoidable solvent use to isolate the molecular entities in high purity. The recovered complexes retain structure and catalytic efficacy, and a library of twenty-four known and unknown PAs are isolated in very good to excellent yields. The scope and limitations of this method are presented.

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Submitted date: 7 September 2023
Accepted/In Press date: 8 January 2024
e-pub ahead of print date: 9 January 2024
Published date: 9 January 2024
Additional Information: Funding Information: GAJ thanks Imam Muhammed Ibn Saud University for offering financial support for a PhD fellowship. GEK thanks the EPSRC UK National Crystallography Service at the University of Southampton for collecting the crystallographic data.49 GEK/ER acknowledge financial support from RSC Research Enablement Grant (E22-9127990267). AM, GEK, JS are grateful to the University of Sussex for HEIF Business Collaboration & Commercialisation 2023 funding. We thank Prof. Louise C. Serpell and Dr Youssra Al-Hilaly (Sussex Neuroscience) for accessing the Circular Dichroism apparatus. We acknowledge REACH Separations Ltd in Biocity Nottingham for chirality determination of the products.

Identifiers

Local EPrints ID: 486844
URI: http://eprints.soton.ac.uk/id/eprint/486844
PURE UUID: 4cec79f5-678a-4d46-975a-1b73f284877e
ORCID for Graham J. Tizzard: ORCID iD orcid.org/0000-0002-1577-5779
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 06 Feb 2024 18:40
Last modified: 13 Apr 2024 01:37

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Contributors

Author: Ghadah Abdullah S. Al Jomeh
Author: Andrew McGown
Author: Emma Richards
Author: Simon J. Coles ORCID iD
Author: Ramón González-Méndez
Author: Chris Dadswell
Author: John Spencer
Author: George E. Kostakis

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