Recent advancement in copper-catalyzed asymmetric reactions of alkynes

Shah, Sadhna; Das, Braja Gopal; Singh, Vinod K.

doi:10.1016/j.tet.2021.132238

Cited by 23 publications

(18 citation statements)

References 180 publications

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“…Several reviews discuss the role of the metal salts and organic ligands [73][74][75][76][77][78][79] and address catalyst design parameters. These include operational stability and a partially saturated coordination environment fulfilled by ligands bearing two or three heteroatoms.…”

Section: Trial Experiments Includementioning

confidence: 99%

Metal-Catalysed A3 Coupling Methodologies: Classification and Visualisation

2022

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The multicomponent reaction of aldehydes, amines, and alkynes, known as A3 coupling, yields propargylamines, a valuable organic scaffold, and has received significant interest and attention in the last years. In order to fully realise the potential of the metal-based catalytic protocols that facilitate this transformation, we summarise substrates, in situ and well-characterised synthetic methods that provide this scaffold and attempt a monumental classification considering several variables (Metal, Coordinating atom(s), Ligand type and name, in-situ or well-characterised, co-catalyst, catalyst and ligand Loading (mol%), solvent, volume, atmosphere, temperature, microwave, time, yield, selectivity (e.e. d.r.), substrate name, functionality, loading (amines, aldehydes, alkynes), and use of molecular sieves). This pioneering work creates a valuable database that contains 2376 entries and allows us to produce graphs and better visualise their impact on the reaction.

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Section: Trial Experiments Includementioning

confidence: 99%

Metal-Catalysed A3 Coupling Methodologies: Classification and Visualisation

2022

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“…Copper-catalyzed reactions of alkynes have advanced significantly over the past few decades, and several useful reviews have been published on the chemistry of alkynes with copper metal. [33][34][35][36][37][38][39] In recent years, studies have been carried out on catalysts based on mesoporous materials doped with rare earth elements (REEs). In studies devoted to the influence of the promoting activity of various nature metals, in particular, when comparing the activity of REEs and d-elements, it was found that the catalyst doped with REE had the best performance.…”

Section: Introductionmentioning

confidence: 99%

Mesoporous silica gel doped with dysprosium and modified with copper: A selective catalyst for the hydrogenation of 1‐hexyne/1‐hexene mixture

Tokranova

Tokranov

Vinogradov

et al. 2022

Int J of Chemical Kinetics

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The selective hydrogenation of 1-hexyne/1-hexene mixture in the temperature range 100-140 • C and a hydrogen pressure of 3 atm was studied on catalysts based on mesoporous silica gel modified with copper and mesoporous silica gel doped with dysprosium and modified with copper. The physicochemical characteristics of the samples were studied by low temperature nitrogen adsorption-desorption method, scanning electron microscopy (SEM), X-ray fluorescence (XRF), and inductively coupled plasma mass spectrometry (ICP-MS). In addition, theoretical calculations of the entropies and energies of formation of activated complexes of the hydrogenation reactions of 1-hexyne and 1-hexene in the gas phase have been calculated with Gaussian 09 software using the density functional theory (DFT) B3LYP/cc-pVQZ method. It was found that the presence of dysprosium in the structure of mesoporous silica gel leads to an increase in catalytic activity in the hydrogenation of 1-hexyne. Moreover, it was shown that mesoporous silica gel modified with copper has the highest selectivity for hexene-1 in the hydrogenation reaction of 1-hexyne/1-hexene mixture at 130 • C.

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“…Several examples of this approach, including Cu(I)-catalyzed alkynylations of (thio)chromones 24 − 27 and quinolines 13 , 28 and allylic alkylations of terminal alkynes, 29 have been published during the last several years, but the direct Cu(I)-catalyzed alkynylation of quinolones has not been accomplished so far. 30 , 31 …”

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confidence: 99%

“…The limited reactivity of alkyl alkynes and the lack of reactivity of linear alkynes are consistent with the literature observations in other Cu-catalyzed reactions. 31 , 36 , 37 Various quinolones can be used with this catalytic system. Excellent yields were obtained for quinolones both with activating and with deactivating groups present in the quinolone ring ( 3eg – 3ig ) and for those with disubstituted substrates ( 3jg and 3kg ).…”

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confidence: 99%

Cu(I)-Catalyzed Alkynylation of Quinolones

2022

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Herein we report the first alkynylation of quinolones with terminal alkynes under mild reaction conditions. The reaction is catalyzed by Cu(I) salts in the presence of a Lewis acid, which is essential for the reactivity of the system. The enantioselective version of this transformation has also been explored, and the methodology has been applied in the synthesis of the enantioenriched tetrahydroquinoline alkaloid cuspareine.

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Recent advancement in copper-catalyzed asymmetric reactions of alkynes

Cited by 23 publications

References 180 publications

Metal-Catalysed A3 Coupling Methodologies: Classification and Visualisation

Metal-Catalysed A3 Coupling Methodologies: Classification and Visualisation

Mesoporous silica gel doped with dysprosium and modified with copper: A selective catalyst for the hydrogenation of 1‐hexyne/1‐hexene mixture

Cu(I)-Catalyzed Alkynylation of Quinolones

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