Immobilized Gold Nanoparticles Prepared from Gold(III)-Containing Ionic Liquids on Silica: Application to the Sustainable Synthesis of Propargylamines
A cycloaurated phosphinothioic amide gold(III) complex was supported on amorphous silica with the aid of an imidazolium ionic liquid (IL) physisorbed in the SiO<sub>2</sub> pores (SiO<sub>2</sub>⁻IL) and covalently bonded to the SiO<sub>2</sub> (SiO<s...
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| Format: | Article |
| Language: | English |
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MDPI AG
2018-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/23/11/2975 |
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| author | Raquel Soengas Yolanda Navarro María José Iglesias Fernando López-Ortiz |
| author_facet | Raquel Soengas Yolanda Navarro María José Iglesias Fernando López-Ortiz |
| author_sort | Raquel Soengas |
| collection | DOAJ |
| description | A cycloaurated phosphinothioic amide gold(III) complex was supported on amorphous silica with the aid of an imidazolium ionic liquid (IL) physisorbed in the SiO<sub>2</sub> pores (SiO<sub>2</sub>⁻IL) and covalently bonded to the SiO<sub>2</sub> (SiO<sub>2</sub>@IL). Gold(0) nanoparticles (AuNPs) were formed in situ and subsequently immobilized on the SiO<sub>2</sub>⁻IL/SiO<sub>2</sub>@IL phase. The resulting catalytic systems Au⁻SiO<sub>2</sub>⁻IL and Au⁻SiO<sub>2</sub>@IL promoted the solvent-free A<sup>3</sup> 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⁻SiO<sub>2</sub>@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, <sup>31</sup>P high resolution magic angle spinning (HRMAS) NMR spectroscopy is introduced as a simple technique to establish the Au loading of the catalyst. |
| first_indexed | 2024-04-12T01:59:16Z |
| format | Article |
| id | doaj.art-70b0ecd82a6446babe7e40bd3c1c6234 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-12T01:59:16Z |
| publishDate | 2018-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-70b0ecd82a6446babe7e40bd3c1c62342022-12-22T03:52:43ZengMDPI AGMolecules1420-30492018-11-012311297510.3390/molecules23112975molecules23112975Immobilized Gold Nanoparticles Prepared from Gold(III)-Containing Ionic Liquids on Silica: Application to the Sustainable Synthesis of PropargylaminesRaquel Soengas0Yolanda Navarro1María José Iglesias2Fernando López-Ortiz3Área de Química Orgánica, Research Centre CIAIMBITAL, Universidad de Almería, Carretera de Sacramento s/n, 04120 Almería, SpainÁrea de Química Orgánica, Research Centre CIAIMBITAL, Universidad de Almería, Carretera de Sacramento s/n, 04120 Almería, SpainÁrea de Química Orgánica, Research Centre CIAIMBITAL, Universidad de Almería, Carretera de Sacramento s/n, 04120 Almería, SpainÁrea de Química Orgánica, Research Centre CIAIMBITAL, Universidad de Almería, Carretera de Sacramento s/n, 04120 Almería, SpainA cycloaurated phosphinothioic amide gold(III) complex was supported on amorphous silica with the aid of an imidazolium ionic liquid (IL) physisorbed in the SiO<sub>2</sub> pores (SiO<sub>2</sub>⁻IL) and covalently bonded to the SiO<sub>2</sub> (SiO<sub>2</sub>@IL). Gold(0) nanoparticles (AuNPs) were formed in situ and subsequently immobilized on the SiO<sub>2</sub>⁻IL/SiO<sub>2</sub>@IL phase. The resulting catalytic systems Au⁻SiO<sub>2</sub>⁻IL and Au⁻SiO<sub>2</sub>@IL promoted the solvent-free A<sup>3</sup> 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⁻SiO<sub>2</sub>@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, <sup>31</sup>P high resolution magic angle spinning (HRMAS) NMR spectroscopy is introduced as a simple technique to establish the Au loading of the catalyst.https://www.mdpi.com/1420-3049/23/11/2975goldnanoparticlesmulticomponent reactionsupported catalystpropargylamineHRMAS |
| spellingShingle | Raquel Soengas Yolanda Navarro María José Iglesias Fernando López-Ortiz Immobilized Gold Nanoparticles Prepared from Gold(III)-Containing Ionic Liquids on Silica: Application to the Sustainable Synthesis of Propargylamines Molecules gold nanoparticles multicomponent reaction supported catalyst propargylamine HRMAS |
| title | Immobilized Gold Nanoparticles Prepared from Gold(III)-Containing Ionic Liquids on Silica: Application to the Sustainable Synthesis of Propargylamines |
| title_full | Immobilized Gold Nanoparticles Prepared from Gold(III)-Containing Ionic Liquids on Silica: Application to the Sustainable Synthesis of Propargylamines |
| title_fullStr | Immobilized Gold Nanoparticles Prepared from Gold(III)-Containing Ionic Liquids on Silica: Application to the Sustainable Synthesis of Propargylamines |
| title_full_unstemmed | Immobilized Gold Nanoparticles Prepared from Gold(III)-Containing Ionic Liquids on Silica: Application to the Sustainable Synthesis of Propargylamines |
| title_short | Immobilized Gold Nanoparticles Prepared from Gold(III)-Containing Ionic Liquids on Silica: Application to the Sustainable Synthesis of Propargylamines |
| title_sort | immobilized gold nanoparticles prepared from gold iii containing ionic liquids on silica application to the sustainable synthesis of propargylamines |
| topic | gold nanoparticles multicomponent reaction supported catalyst propargylamine HRMAS |
| url | https://www.mdpi.com/1420-3049/23/11/2975 |
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