Recent advances in copper-catalyzed imine-based multicomponent reactions

Innocenti, Riccardo; Lenci, Elena; Trabocchi, Andrea

doi:10.1016/j.tetlet.2020.152083

Cited by 16 publications

(3 citation statements)

References 71 publications

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“…The C-H activation has gained significant interest and represents one of the eighth main research milestones [21][22][23]. Similarly, imines and enamines are essential components for several organic transformations and organic scaffolds of high interest [24][25][26][27][28][29]. The A 3 coupling reaction forms a new C-C σ bond via C-H activation of a terminal alkyne and yields PAs in one step with one water molecule as a by-product.…”

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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“…Moreover, multicomponent reactions (MCRs) are synthetic protocols which are able to join three or more substrates together in a highly regio-and stereoselective manner in order to deliver the structurally complex organic molecules. Accordingly, it is worth mentioning that they have been remarkably applied in all elds of organic synthesis 7,12,[28][29][30][31] . But, regarding the one pot synthesis, they give yield in a highly stereoselective manner which is useful for the organic transformations [32][33][34] .…”

Section: Introductionmentioning

confidence: 99%

Silver Coordination-Polymer based of 4,6-Diamino-2-pyrimidinethiol as Organic Ligand: a Highly Reusable Heterogeneous Nanocatalyst for the Asymmetric Hantzsch Synthesis of Polyhydroquinolines under Green Conditions

Hussain-Khil¹,

Ghorbani‐Choghamarani²,

Mohammadi³

2021

Preprint

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A highly efficient and stable heterogeneous coordination polymer (CP) was successfully prepared by hydrothermal combination of silver and 4,6-diamino-2-pyrimidinethiol. The prepared coordination polymer was characterized by FT-IR, XRD, TGA, SEM, EDX, X-ray mapping and Nitrogen adsorption-desorption analysis. The prepared Ag-CP exhibit excellent catalytic activity in multicomponent Hantzsch synthesis of polyhydroquinolines under mild reaction conditions in relatively short reaction times. The heterogeneity of the catalyst was confirmed by the hot filtration test; also, the catalyst was reused for at least four times under the optimized reaction conditions without any significant loss of its catalytic activity.

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“…23 Various tandem processes, employing the capture of intermediately formed vinylcopper derivatives, have also been devised. 24 Scheme 1 Cu-catalyzed hydroboration The optimal performance of Cu catalyst is achieved by the addition of an activator, which generates Cu species capable of undergoing efficient transmetalation with B 2 Pin 2 (Scheme 1B). The most used activators are air-and moisture-sensitive alkali metal tert-butoxides, though some other basic systems, most notably KOAc-LiCl, 17a,b were identified.…”

mentioning

confidence: 99%

Alumina-Promoted Copper-Catalyzed Hydroboration of Alkynes

Latyshev,

Barashkova,

Parulava

et al. 2024

Synthesis

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Alumina was found to activate Cu(I) catalysts in hydroboration of alkynes. This allowed us to develop a simple and efficient protocol for hydroboration of alkynes with B2Pin2 using inexpensive CuCl/PPh3 catalytic system. The approach does not require moisture-sensitive activators and stepwise preparation of “activated” Cu complex. The developed conditions were applied to the preparation of β-styrylboronates from terminal and internal alkynes with excellent regio- and stereoselectivity. The procedure can also be extended to other terminal alkynes by the appropriate choice of ligand.

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Recent advances in copper-catalyzed imine-based multicomponent reactions

Cited by 16 publications

References 71 publications

Metal-Catalysed A3 Coupling Methodologies: Classification and Visualisation

Metal-Catalysed A3 Coupling Methodologies: Classification and Visualisation

Silver Coordination-Polymer based of 4,6-Diamino-2-pyrimidinethiol as Organic Ligand: a Highly Reusable Heterogeneous Nanocatalyst for the Asymmetric Hantzsch Synthesis of Polyhydroquinolines under Green Conditions

Alumina-Promoted Copper-Catalyzed Hydroboration of Alkynes

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