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Title: 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.

Authors:
ORCiD logo; ; ;
Publication Date:
Sponsoring Org.:
USDOE Office of Energy Efficiency and Renewable Energy (EERE), Federal Energy Management Program Office (EE-5F)
OSTI Identifier:
1482141
Grant/Contract Number:  
CTQ2014- 57157-P
Resource Type:
Journal Article: 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. doi: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. doi: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},
issn = {1420-3049},
number = 11,
volume = 23,
place = {Switzerland},
year = {2018},
month = {11}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record at 10.3390/molecules23112975

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Works referenced in this record:

Chemoselective Hydrogenation of Nitro Compounds with Supported Gold Catalysts
journal, July 2006