Single and double A3-coupling (aldehyde-amine-alkyne) reaction catalyzed by an air stable copper(I)-phosphole complex

Cammarata, Jose; Rivera, Rocío Melissa; Fuentes, Franmerly; Otero, Yomaira; Ocando-Mavárez, Edgar; Arce, Alejandro J.; García, Juan Manuel Vicent

doi:10.1016/j.tetlet.2017.09.031

Cited by 45 publications

(26 citation statements)

References 40 publications

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“…A novel tetrameric Cu(I) complex 13 containing tert ‐butyl‐diallylphosphane ligand was introduced by Garcia et al The tetrameric complex 13 was effectively utilized for the synthesis of propargylamines under solvent‐free mild conditions. In parallel, the same group prepared another air‐stable Cu(I)phosphole complex 14 (Scheme a) . The bis‐propargylamines 17 were synthesized employing the Cu(I)phosphole catalyst 14 (Scheme b) .…”

Section: Homogeneous Metal Catalysis For A3 Coupling Reactionsmentioning

confidence: 99%

“…In parallel, the same group prepared another air‐stable Cu(I)phosphole complex 14 (Scheme a) . The bis‐propargylamines 17 were synthesized employing the Cu(I)phosphole catalyst 14 (Scheme b) . In a recent study, Balakrishna et al efficiently applied copper(I)complex [{Cu(µ‐I) 2 Cu}(PPh 3 ) 4 ] 15 under microwave irradiation …”

Section: Homogeneous Metal Catalysis For A3 Coupling Reactionsmentioning

confidence: 99%

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Recent Advances in the A³ Coupling Reactions and their Applications

2019

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Propargylamines are an important class of organic compounds that have been widely used as building blocks for the synthesis of various kinds of chemically and biologically relevant compounds. Over the last few years, there have been a rapid growth in the research dedicated to developing the synthetic protocol for propargylamine derivatives. Among various methods that are reported for the synthesis of propargylamines, the three‐component coupling of aldehyde, amine and alkyne (commonly termed as A3 coupling reactions) secured a special place because of its convenient/atom economical approach and thus broadly used by researchers. Our aim in this review is to highlight the most recent advancement on A3 coupling reactions for the synthesis of various propargylamine derivatives as well as on the developments of subsequent transformation of these compounds to useful heterocyclic compounds and the related products.

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Section: Homogeneous Metal Catalysis For A3 Coupling Reactionsmentioning

confidence: 99%

Section: Homogeneous Metal Catalysis For A3 Coupling Reactionsmentioning

confidence: 99%

Recent Advances in the A³ Coupling Reactions and their Applications

2019

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“…The photophysical studies showed that all complexes exhibit fluorescence with quantum yields Φf = 0.04 -0.11, being the highest value for complex 2b. These new complexes open up the possibility of new researches in catalytic applications or studies of their biological activitiesas we have previously reported[16,44].…”

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confidence: 89%

Synthesis, Characterization and Photophysical Properties of a New 2,5-Di(aryl)phosphole Derivative and Their Trigonal Copper-Phosphole Complexes

Rios¹,

Fuentes²,

Garfido

et al. 2020

Preprint

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<div>A new phosphole derivative 2,5-di(2-quinolyl)-1-phenylphosphole (1) was synthesized by using the Fagan-Nugent method. Phosphole was obtained as an air stable solid in high yield (73%). Additionally, two new copper phosphole complexes [CuX(Phosphole)2] (X = Cl (2a), I (2b), Phosphole = 1) have been synthesized by reaction of CuX (X = Cl, I) and phosphole derivative (1). All compound were characterized by NMR, ESI-MS, UV–Vis and fluorescence spectroscopy. The photophysical properties of all compounds were analyzed, UV-Vis spectra of the complexes 2a-b shown π–π* transitions with shift very similar to the found in the free phosphole due to that their symmetrical structures inhibits efficient ILCT. We have found that the compounds 1, 2a-b exhibited fluorescence between 460 and 583 nm with quantum yields of Φf = 0.04 – 0.11. The emission energy of 2b is higher than 2a, suggesting that λmax is affected by the ligand-field strength of the halogen ions in the complexes (I- < Cl- ).</div>

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“…An alternative atom-economical procedure for the synthesis of propargylamines is the one-pot, three-component, metal-catalyzed reaction of an alkyne, an aldehyde, and an amine, the so-called A 3 coupling [ 7 ]. Homogeneous catalysts based on a large number of transition metal ions have been used for the A 3 coupling reaction, including Cu [ 8 , 9 , 10 , 11 , 12 ], Ag [ 13 , 14 , 15 , 16 ], Cu/Ru bimetallic systems [ 17 , 18 ], Zn [ 19 , 20 , 21 ], Fe [ 22 , 23 ], In [ 24 , 25 ], Ir [ 26 , 27 ], Hg [ 28 ], Ni [ 29 ], Rh [ 30 ], Mn [ 31 ], Co [ 32 ], Bi [ 33 ], and Cd [ 34 ]. Over the past few years, increasing attention has been paid to the catalytic performance of Au in promoting the A 3 coupling reaction, including Au(I) and Au(III) salts and organic Au complexes [ 35 , 36 , 37 , 38 ].…”

Section: Introductionmentioning

confidence: 99%

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

Soengas¹,

Navarro²,

Iglesias³

et al. 2018

Molecules

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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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Single and double A3-coupling (aldehyde-amine-alkyne) reaction catalyzed by an air stable copper(I)-phosphole complex

Cited by 45 publications

References 40 publications

Recent Advances in the A³ Coupling Reactions and their Applications

Recent Advances in the A³ Coupling Reactions and their Applications

Synthesis, Characterization and Photophysical Properties of a New 2,5-Di(aryl)phosphole Derivative and Their Trigonal Copper-Phosphole Complexes

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

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Single and double A3-coupling (aldehyde-amine-alkyne) reaction catalyzed by an air stable copper(I)-phosphole complex

Cited by 45 publications

References 40 publications

Recent Advances in the A3 Coupling Reactions and their Applications

Recent Advances in the A3 Coupling Reactions and their Applications

Synthesis, Characterization and Photophysical Properties of a New 2,5-Di(aryl)phosphole Derivative and Their Trigonal Copper-Phosphole Complexes

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

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Recent Advances in the A³ Coupling Reactions and their Applications

Recent Advances in the A³ Coupling Reactions and their Applications