A novel tetramer copper(I) complex containing diallylphosphine ligands: Synthesis, characterization and catalytic application in A3-coupling (Aldehyde-Amine-Alkyne) reactions

Rosales, Jennifer; García, Juan Manuel Vicent; Ávila, Edward E.; González, Teresa; Coll, David S.; Ocando-Mavárez, Edgar

doi:10.1016/j.ica.2017.07.038

Cited by 16 publications

(8 citation statements)

References 109 publications

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“…Later, Liao et al fabricated a dicopper complex 12 for the A 3 coupling reactions effectively. 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) .…”

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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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%

Recent Advances in the A³ Coupling Reactions and their Applications

2019

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“…This reaction has been extensively studied in the context of homogeneous catalysis since the 2000s and the seminal work of the Li group with the use of inorganic salts of various metals, including gold, silver, and copper. − Thereafter, different systems were developed to improve the process, including transition metal complexes as homogeneous catalysts. − …”

Section: Introductionmentioning

confidence: 99%

Amine-Functionalized Mesoporous Silica as a Support for on-Demand Release of Copper in the A³-Coupling Reaction: Ultralow Concentration Catalysis and Confinement Effect

Terra

Moores

Moura

2019

ACS Sustainable Chem. Eng.

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The study of catalysts activity at ultralow concentration is of prime importance for the development of more sustainable catalytic processes. In this work, we designed a mesoporous MCM-41 silica with covalent functionalization with amine groups at different levels of coverage. This material was used as a support to immobilize small quantities of Cu(I) species to be used as a catalyst in the A3-coupling reaction. The support design allowed controlled release of the catalytically active species as well as its scavenging after reaction. This system achieved excellent catalytic performance, leading to 95% yield of the desired propargylamine within 2 h of reaction at 100 °C under microwave conditions, using only 0.02 mol % of catalyst, the lowest catalyst amount ever reported for this reaction and high TON (4750) and TOF (2375 h–1). An interesting effect was noticed, where the catalyst on the support yielded improved reaction rates as compared to unsupported catalysts in solution under the same concentration conditions. We discuss the possibility of a confinement of metal species inside the mesoporous structure of the support, which made the immobilized system more effective than its homogeneous counterpart. The present study pushes the limits of A3-coupling reaction conditions and the potential of supported metal catalysis.

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“…In 2017, the first use of a tetrametallic Cu(I) complex to promote the A 3 coupling was reported by Garcia and Ocando-Mavárez [116]. The authors synthesised and characterised a copper(I) complex with tert-butyldiallylphosphine ligands.…”

Section: Yield 50%mentioning

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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A novel tetramer copper(I) complex containing diallylphosphine ligands: Synthesis, characterization and catalytic application in A3-coupling (Aldehyde-Amine-Alkyne) reactions

Cited by 16 publications

References 109 publications

Recent Advances in the A³ Coupling Reactions and their Applications

Recent Advances in the A³ Coupling Reactions and their Applications

Amine-Functionalized Mesoporous Silica as a Support for on-Demand Release of Copper in the A³-Coupling Reaction: Ultralow Concentration Catalysis and Confinement Effect

Metal-Catalysed A3 Coupling Methodologies: Classification and Visualisation

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A novel tetramer copper(I) complex containing diallylphosphine ligands: Synthesis, characterization and catalytic application in A3-coupling (Aldehyde-Amine-Alkyne) reactions

Cited by 16 publications

References 109 publications

Recent Advances in the A3 Coupling Reactions and their Applications

Recent Advances in the A3 Coupling Reactions and their Applications

Amine-Functionalized Mesoporous Silica as a Support for on-Demand Release of Copper in the A3-Coupling Reaction: Ultralow Concentration Catalysis and Confinement Effect

Metal-Catalysed A3 Coupling Methodologies: Classification and Visualisation

Contact Info

Product

Resources

About

Recent Advances in the A³ Coupling Reactions and their Applications

Recent Advances in the A³ Coupling Reactions and their Applications

Amine-Functionalized Mesoporous Silica as a Support for on-Demand Release of Copper in the A³-Coupling Reaction: Ultralow Concentration Catalysis and Confinement Effect