Immobilized Gold Nanoparticles Prepared from Gold(III)-Containing Ionic Liquids on Silica: Application to the Sustainable Synthesis of Propargylamines
Abstract
A cycloaurated phosphinothioic amide gold(III) complex was supported on amorphous silica with the aid of an imidazolium ionic liquid (IL) physisorbed in the SiO2 pores (SiO2–IL) and covalently bonded to the SiO2 (SiO2@IL). Gold(0) nanoparticles (AuNPs) were formed in situ and subsequently immobilized on the SiO2–IL/SiO2@IL phase. The resulting catalytic systems Au–SiO2–IL and Au–SiO2@IL promoted the solvent-free A3 coupling reaction of alkynes, aldehydes, and amines in high yields under solvent-free conditions with very low catalyst loading and without the use of additives. The Au–SiO2@IL catalyst showed good recyclability and could be reused at least five times with yields of propargylamines of ≥80%. This synthetic method provides a green and low cost way to effectively prepare propargylamines. Additionally, 31P high resolution magic angle spinning (HRMAS) NMR spectroscopy is introduced as a simple technique to establish the Au loading of the catalyst.
- Publication Date:
- Sponsoring Org.:
- USDOE Office of Energy Efficiency and Renewable Energy (EERE), Energy Efficiency Office. Federal Energy Management Program Office
- OSTI Identifier:
- 1482141
- Grant/Contract Number:
- CTQ2014- 57157-P
- Resource Type:
- Published Article
- Journal Name:
- Molecules
- Additional Journal Information:
- Journal Name: Molecules Journal Volume: 23 Journal Issue: 11; Journal ID: ISSN 1420-3049
- Publisher:
- MDPI AG
- Country of Publication:
- Switzerland
- Language:
- English
Citation Formats
Soengas, Raquel, Navarro, Yolanda, Iglesias, María, and López-Ortiz, Fernando. Immobilized Gold Nanoparticles Prepared from Gold(III)-Containing Ionic Liquids on Silica: Application to the Sustainable Synthesis of Propargylamines. Switzerland: N. p., 2018.
Web. doi:10.3390/molecules23112975.
Soengas, Raquel, Navarro, Yolanda, Iglesias, María, & López-Ortiz, Fernando. Immobilized Gold Nanoparticles Prepared from Gold(III)-Containing Ionic Liquids on Silica: Application to the Sustainable Synthesis of Propargylamines. Switzerland. https://doi.org/10.3390/molecules23112975
Soengas, Raquel, Navarro, Yolanda, Iglesias, María, and López-Ortiz, Fernando. Wed .
"Immobilized Gold Nanoparticles Prepared from Gold(III)-Containing Ionic Liquids on Silica: Application to the Sustainable Synthesis of Propargylamines". Switzerland. https://doi.org/10.3390/molecules23112975.
@article{osti_1482141,
title = {Immobilized Gold Nanoparticles Prepared from Gold(III)-Containing Ionic Liquids on Silica: Application to the Sustainable Synthesis of Propargylamines},
author = {Soengas, Raquel and Navarro, Yolanda and Iglesias, María and López-Ortiz, Fernando},
abstractNote = {A cycloaurated phosphinothioic amide gold(III) complex was supported on amorphous silica with the aid of an imidazolium ionic liquid (IL) physisorbed in the SiO2 pores (SiO2–IL) and covalently bonded to the SiO2 (SiO2@IL). Gold(0) nanoparticles (AuNPs) were formed in situ and subsequently immobilized on the SiO2–IL/SiO2@IL phase. The resulting catalytic systems Au–SiO2–IL and Au–SiO2@IL promoted the solvent-free A3 coupling reaction of alkynes, aldehydes, and amines in high yields under solvent-free conditions with very low catalyst loading and without the use of additives. The Au–SiO2@IL catalyst showed good recyclability and could be reused at least five times with yields of propargylamines of ≥80%. This synthetic method provides a green and low cost way to effectively prepare propargylamines. Additionally, 31P high resolution magic angle spinning (HRMAS) NMR spectroscopy is introduced as a simple technique to establish the Au loading of the catalyst.},
doi = {10.3390/molecules23112975},
journal = {Molecules},
number = 11,
volume = 23,
place = {Switzerland},
year = {2018},
month = {11}
}
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