Thiolate-protected Gold Nanoclusters Au<sub>25</sub>(phenylethanethiol)<sub>18</sub>: An Efficient Catalyst for the Synthesis of Propargylamines from Aldehydes, Amines, and Alkynes

Adachi, Yurina; Kawasaki, Hideya; Nagata, Tatsuki; Obora, Yasushi

doi:10.1246/cl.160813

Cited by 31 publications

(17 citation statements)

References 65 publications

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“…Further investigation into the nature of catalytic gold species involved the use of fluorine-tagged NHC complexes and TEM analysis of the reaction mixtures, which revealed the presence of gold nanoparticles. Taken together, the lack of chiral induction, the similar reaction profiles and the observation of gold nanoparticles lends credence to the notion that the A 3 -reactions discussed in this study may in fact be promoted by gold nanoparticles, 85,91,92 as depicted in Scheme 9, that are formed from the gold complexes added as catalysts. This implies that a wide range of gold complexes might act as suitable precatalysts, but would have very significant ramifications for attempting to generate three-component enantioselective A 3 coupling methodology based on such gold complexes.…”

Section: Discussionsupporting

confidence: 78%

Some insights into the gold-catalysed A 3 -coupling reaction

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Brisdon

Randall

et al. 2017

Journal of Organometallic Chemistry

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Abstract.A series of cyclometallated and functionalised NHC gold(I) and gold(III) complexes, many of which feature chiral ligands, and their application to A 3 -coupling reactions is presented. Gold(III) complexes were found to be particularly effective catalysts for the coupling in a range of solvents, however no asymmetric induction was obtained when using chiral gold complexes and the rate of product formation was found to be similar even when using different ligand systems. In-situ NMR analysis of these reactions indicates that decomposition of the catalyst occurs during the course of the reaction while TEM studies revealed the presence of gold nanoparticles in crude reaction mixtures. Taken together these data suggest that the gold nanoparticales, rather than the intact gold complexes, could be the catalytically active species, and if so this may have significant implications for other gold-catalysed systems.Dedicated to Dr. Mark Whiteley (an outstanding colleague) on his retirement from the School of Chemistry, University of Manchester.

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Section: Discussionsupporting

confidence: 78%

Some insights into the gold-catalysed A 3 -coupling reaction

Price

Brisdon

Randall

et al. 2017

Journal of Organometallic Chemistry

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“…In 2016, Obora and co‐workers prepared phenylethanethiol‐protected colloidal Au nanoclusters [Au 25 (PET) 18 ] . The Au 25 (PET) 18 as an efficient catalyst can be used in eco‐friendly, low‐toxicity, efficient A 3 coupling of a range of aldehydes, amines and alkynes to give the propargylamine derivatives in excellent yields (Scheme ).…”

Section: The Various Catalytic Systems For A3 Coupling Reactionsmentioning

confidence: 99%

“…It is important to stress that despite huge advancements of the reported works in the literature, another important challenges in the A 3 coupling reactions is nature of solvent and kind of the catalyst. A number of nanocatalysts, including copper, silver, gold, nickel, magnetic nanocatalysts and Co 3 O 4 , ZnS and nanopowder zinc titanate were successfully applied for A 3 coupling reactions with yields ranging from good to excellent in appropriate times in organic solvents or aqueous medium . The authors ascribed high catalytic activity of nanocatalysts to the particles size.…”

Section: Outlook and Conclusionmentioning

confidence: 99%

A Review on Recent Advances in the Application of Nanocatalysts in A³ Coupling Reactions

Nasrollahzadeh

Sajjadi

Ghorbannezhad

et al. 2018

The Chemical Record

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A coupling is one of the few transition-metal catalyzed carbon-carbon bond forming reactions that have been established as a most direct, efficient and atom-economical synthetic approach to afford propargylamine derivatives using various catalysts. A large number of nanosized heterogeneous catalysts for three-component coupling reactions between an aldehyde, an amine, and a terminal alkyne have been popularly introduced as an A coupling in the last decade. The coupling product has found a broad application as a key intermediate for a variety of heterocyclic useful compounds and numerous biologically active molecules such as β-lactams, conformationally restricted peptides, isosteres, herbicides, fungicides, indolizines, pyrroles, quinolines and therapeutic drug molecules. This review aims to give an overview of the current progress made towards the preparation and application of various nanocatalysts-catalyzed A coupling transformations for the synthesis of propargylamines from 2007 to 2017. Several nanocatalysts based on metal and metal oxide nanoparticles (NPs) such as copper, gold, silver, iron, nickel, cobalt and zinc have successfully been employed in A coupling reactions. Besides, core-shells NPs, polymers, complexes, graphenes, metal-organic frameworks and ionic liquids have also been used in these reactions. Abundant examples have been given in this area. Different aspects of the reactions, disparate methods of preparation of nanocatalysts, characterization and their reusability have been perused.

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“…Despite the high efficiency of the reported catalysts, in many cases high catalyst loading and the expensive price of gold considerably limit the versatility of these catalytic systems. Along this line, recently, different heterogeneous gold as well as magnetic catalysts have been applied for the A 3 coupling reaction. Herein we report for the first time the use of caffeine as a naturally occurring and cheap compound for the modification of magnetic NPs and for the stabilization of gold metal.…”

Section: Introductionmentioning

confidence: 99%

Caffeine gold complex supported on magnetic nanoparticles as a green and high turnover frequency catalyst for room temperature A³ coupling reaction in water

Gholinejad

Afrasi

Nájera

2019

Applied Organom Chemis

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A new heterogeneous catalyst derived from gold (III) and supported on caffeine‐coated magnetic nanoparticles, Fe3O4@Caff‐Au, has been prepared and characterized using different techniques. This magnetic gold composite shows high catalytic activity in A3 coupling reactions of terminal alkynes, aldehydes and secondary amines. Using this green catalyst, propargylamines are obtained in high turnover frequency in short reaction times using water as solvent at room temperature. This stable and ready accessible catalyst can be easily recycled magnetically for at least nine consecutive runs without significant loss of activity and with slight aggregation of Au species.

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Thiolate-protected Gold Nanoclusters Au₂₅(phenylethanethiol)₁₈: An Efficient Catalyst for the Synthesis of Propargylamines from Aldehydes, Amines, and Alkynes

Cited by 31 publications

References 65 publications

Some insights into the gold-catalysed A 3 -coupling reaction

Some insights into the gold-catalysed A 3 -coupling reaction

A Review on Recent Advances in the Application of Nanocatalysts in A³ Coupling Reactions

Caffeine gold complex supported on magnetic nanoparticles as a green and high turnover frequency catalyst for room temperature A³ coupling reaction in water

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Thiolate-protected Gold Nanoclusters Au25(phenylethanethiol)18: An Efficient Catalyst for the Synthesis of Propargylamines from Aldehydes, Amines, and Alkynes

Cited by 31 publications

References 65 publications

Some insights into the gold-catalysed A 3 -coupling reaction

Some insights into the gold-catalysed A 3 -coupling reaction

A Review on Recent Advances in the Application of Nanocatalysts in A3 Coupling Reactions

Caffeine gold complex supported on magnetic nanoparticles as a green and high turnover frequency catalyst for room temperature A3 coupling reaction in water

Contact Info

Product

Resources

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Thiolate-protected Gold Nanoclusters Au₂₅(phenylethanethiol)₁₈: An Efficient Catalyst for the Synthesis of Propargylamines from Aldehydes, Amines, and Alkynes

A Review on Recent Advances in the Application of Nanocatalysts in A³ Coupling Reactions

Caffeine gold complex supported on magnetic nanoparticles as a green and high turnover frequency catalyst for room temperature A³ coupling reaction in water