Immobilized Gold Nanoparticles Prepared from Gold(III)-Containing Ionic Liquids on Silica: Application to the Sustainable Synthesis of Propargylamines

Soengas, Raquel; Navarro, Yolanda; Iglesias, María; López-Ortiz, Fernando

doi:10.3390/molecules23112975

Title: Immobilized Gold Nanoparticles Prepared from Gold(III)-Containing Ionic Liquids on Silica: Application to the Sustainable Synthesis of Propargylamines

Journal Article · 14 November 2018 · Molecules

DOI: https://doi.org/10.3390/molecules23112975 · OSTI ID:1482141

; Navarro, Yolanda; Iglesias, María; López-Ortiz, Fernando

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.

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Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Energy Efficiency Office. Federal Energy Management Program Office

Grant/Contract Number:: CTQ2014- 57157-P

OSTI ID:: 1482141

Journal Information:: Molecules, Journal Name: Molecules Vol. 23 Journal Issue: 11; ISSN 1420-3049

Publisher:: MDPI AGCopyright Statement

Country of Publication:: Switzerland

Language:: English

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Cited by: 15 works

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Ionic liquids in biotechnology and beyond Claus, Johanna; Sommer, Fridolin O.; Kragl, Udo Solid State Ionics, Vol. 314 https://doi.org/10.1016/j.ssi.2017.11.012	journal	January 2018
14N NMR and Two-Dimensional Suspension1H and13C HRMAS NMR Spectroscopy of Ionic Liquids Immobilized on Silica Brenna, Stefano; Posset, Tobias; Furrer, Julien Chemistry - A European Journal, Vol. 12, Issue 10 https://doi.org/10.1002/chem.200501193	journal	March 2006
Supported Au/MIL-53(Al): a reusable green solid catalyst for the three-component coupling reaction of aldehyde, alkyne, and amine Liu, Lili; Tai, Xishi; Zhang, Nana Reaction Kinetics, Mechanisms and Catalysis, Vol. 119, Issue 1 https://doi.org/10.1007/s11144-016-1034-5	journal	April 2016

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