The Asymmetric A3(Aldehyde–Alkyne–Amine) Coupling: Highly Enantioselective Access to Propargylamines

Mo, Jia‐Nan; Su, Junqi; Zhao, Jiannan

doi:10.3390/molecules24071216

Cited by 45 publications

(21 citation statements)

References 72 publications

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“…Several excellent reviews and monographs on the A 3 coupling reaction were published in the literature in recent years. Many of them highlight the advances in the synthesis of propargylamines, [23] including the asymmetric version of the reaction [17g,23c,24] . Besides, a number of reviews are available on the employment of particular catalysts, e. g ., gold, [25] nanoparticles [26] and so on.…”

Section: Introductionmentioning

confidence: 99%

A³ Coupling Reaction in the Synthesis of Heterocyclic Compounds

2020

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In recent years, the transition‐metal catalyzed three‐component coupling of an aldehyde, an alkyne and an amine, commonly called A3 coupling has become a powerful tool in organic synthesis. The aim of this review is to give a general overview of A3 coupling utility in the synthesis of heterocycles, highlighting the variety of compounds that can be directly accessed from single reactions. The diverse A3 coupling based methodologies that have been developed for the synthesis of N,O,S‐heterocycles are presented, emphasizing the influence of the reaction conditions and the use of additional reagents in the outcome of the transformations.

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Section: Introductionmentioning

confidence: 99%

A³ Coupling Reaction in the Synthesis of Heterocyclic Compounds

2020

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“…However, these reagents are mostly highly moisture-sensitive, and require strictly controlled reaction conditions. One way to form the propargylamines is to apply the transition-metal catalysts in three-component coupling of aldehydes or ketones, amines, and alkynes (A 3coupling [9,13] or KA 2 -coupling [14][15][16] reaction). However, the KA 2 reaction has been largely underdeveloped because of the extremely lower reactivity of ketones.…”

Section: Introductionmentioning

confidence: 99%

“…Traditional methods for preparation of propargylamines include the direct amination of propargyl halides, triflates, phosphates, and acetates . Additionally, these compounds have been prepared through the interaction of the terminal acetylene substrates (with high acidity in C−H bond) with strong bases such as butyllithium, organomagnesium compounds, or LDA to form the alkenyl‐metal reagents. However, these reagents are mostly highly moisture‐sensitive, and require strictly controlled reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

A Novel Recyclable Ni/Cu/Fe Termetallic Nanocatalyst for the Synthesis of Propargylamines through the A³‐Coupling Reactions

et al. 2020

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A novel Ni/Cu/Fe nanocatalyst was prepared via a three‐step procedure for the A3‐coupling reaction of an aldehyde, an amine, and a terminal alkyne to synthesize the corresponding propargylamine. Oleic acid was used in the second step to avoid aggregation of CuFe2O4 nanoparticles. The prepared NiO/OA‐CuFe2O4 (Ni/Cu/Fe) was characterized using X‐ray diffraction (XRD), scanning electron microscopy/wavelength dispersive X‐ray (SEM/WDX), particle size analyzer, fourier transform infrared (FT‐IR) and atomic absorption spectroscopy (AAS). A variety of propargylamines was synthesized using a very small amount of this efficient and inexpensive nanocatalyst in toluene as the solvent at 100 °C. Due to high magnetic properties of the prepared catalyst, its isolation and recycle were very easy, and it was used in five repetitive cycles.

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“…A 3 coupling reactions, i.e. the reactions included alkynes, amines, and aldehydes, first discovered in late 1990s, are one of such examples [30][31][32][33][34][35]. Propargylamines yielded in the A 3 couplings are important intermediates for the synthesis of numerous biologically active heterocyclic compounds, e.g.…”

Section: Introductionmentioning

confidence: 99%

Polymer Beads Decorated with Dendritic Systems as Supports for A3 Coupling Catalysts

et al. 2020

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The gel type microscopic polymer beads bearing epoxy functionalities were modified using the two-stage procedures in order to decorate their surface with the moieties of the zeroth order PAMAM type dendrimer and different heterocyclic aldehydes (2-pyridinecarboxaldehyde, 2-pyrrolidinecarboxaldehyde, furfural or 2-thiophenecarboxaldehyde). The polymeric supports provided in this manner were then used for the immobilization of copper(II) ions. The resulting materials were characterized using different instrumental techniques (optical microscopy, SEM, FTIR microscopy, DR UV–Vis, ICP-OES, and thermal analysis). They were also used as catalysts in the model A3 coupling reaction of benzaldehyde, morpholine and phenylacetylene. The best catalytic activity was found for the polymeric catalyst bearing 2-pyridinecarboxaldehyde moieties. It turned out to be effective in the A3 coupling reactions included different benzaldehyde, alkyne, and secondary amine derivatives, as well. It could also be recycled several times without a significant decrease in its activity in the model A3 coupling reaction. Graphic Abstract

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The Asymmetric A3(Aldehyde–Alkyne–Amine) Coupling: Highly Enantioselective Access to Propargylamines

Cited by 45 publications

References 72 publications

A³ Coupling Reaction in the Synthesis of Heterocyclic Compounds

A³ Coupling Reaction in the Synthesis of Heterocyclic Compounds

A Novel Recyclable Ni/Cu/Fe Termetallic Nanocatalyst for the Synthesis of Propargylamines through the A³‐Coupling Reactions

Polymer Beads Decorated with Dendritic Systems as Supports for A3 Coupling Catalysts

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The Asymmetric A3(Aldehyde–Alkyne–Amine) Coupling: Highly Enantioselective Access to Propargylamines

Cited by 45 publications

References 72 publications

A3 Coupling Reaction in the Synthesis of Heterocyclic Compounds

A3 Coupling Reaction in the Synthesis of Heterocyclic Compounds

A Novel Recyclable Ni/Cu/Fe Termetallic Nanocatalyst for the Synthesis of Propargylamines through the A3‐Coupling Reactions

Polymer Beads Decorated with Dendritic Systems as Supports for A3 Coupling Catalysts

Contact Info

Product

Resources

About

A³ Coupling Reaction in the Synthesis of Heterocyclic Compounds

A³ Coupling Reaction in the Synthesis of Heterocyclic Compounds

A Novel Recyclable Ni/Cu/Fe Termetallic Nanocatalyst for the Synthesis of Propargylamines through the A³‐Coupling Reactions