Combinatorial Synthesis of Acacen-Type Ligands and Their Coordination Compounds

Tomažin, Urša; Grošelj, Uroš; Počkaj, Marta; Požgan, Franc; Štefane, Bogdan; Svete, Jurij

doi:10.1021/acscombsci.7b00027

Cited by 10 publications

(9 citation statements)

References 48 publications

(63 reference statements)

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“…Pilet and co‐workers have prepared and characterized a Ni(II) tetranuclear cubane‐like complex and a mixed Cu(II)‐Dy(III) nonanuclear complex by using a ethanolamine‐derived trifluoromethyl enaminone ligand. Furthermore, the complexes of Cu(II), Ni(II), Co(II) and Pd(II) with different enaminone ligands have also been prepared and clearly identified by Svete and co‐workers . Amazingly, unlike the works on their preparation and characterization, the application of these reported metal‐enaminone complexes as potential catalysts has rarely been investigated.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Synthesis of Enaminone‐Pd(II) Complexes and Their Application in Catalysing Aqueous Suzuki‐Miyaura Cross Coupling Reaction

Cao

Wan

et al. 2020

Chin. J. Chem.

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Summary of main observation and conclusion A series of Pd(II)‐enaminone complexes, termed Pd(eao)2, have been synthesized and characterized. The investigation on the catalytic activities of these new Pd(II)‐reagents has proved that the Pd(eao)2‐1 possesses excellent catalytic activity for the Suzuki‐ Miyaura cross coupling reactions of aryl bromides/chlorides with aryl/vinyl boronic acids in the environmentally benign media of aqueous PEG400 at low loading (5 mol‰). The superiority of this Pd(II)‐reagent to those commercial Pd(II) and Pd(0) catalysts in catalyzing the reactions has been confirmed by parallel experiments. What's more, Pd(eao)2‐2 has been found as a practical catalyst for the homo‐coupling reactions of aryl boronic acids.

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Section: Background and Originality Contentmentioning

confidence: 99%

Synthesis of Enaminone‐Pd(II) Complexes and Their Application in Catalysing Aqueous Suzuki‐Miyaura Cross Coupling Reaction

Cao

Wan

et al. 2020

Chin. J. Chem.

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“…Nevertheless, since a modular and tunable combinatorial synthesis of acacen ligands is available, there is still a lot of potential for improvement of the performance of Cu(II) catalysts based on this class of ligands in CuAIAC reaction (Scheme 20). 32…”

Section: Reactions Catalyzed By Cu(ii)mentioning

confidence: 99%

“…24 On the other hand, Cu(II)-catalyzed CuAIAC reactions take place not only with terminal (cf. Schemes 20, 41, and 42), 32 but also with internal acetylenes (cf. Schemes 3 and 20).…”

Section: Review Syn Thesismentioning

confidence: 99%

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Copper-Catalyzed Azomethine Imine–Alkyne Cycloadditions (CuAIAC)

Grošelj

Požgan²,

Štefane³

et al. 2018

Synthesis

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Although the first example of copper-catalyzed azomethine imine–alkyne cycloaddition (CuAIAC) was published only a year after the seminal papers of Meldal and Sharpless on Cu-catalyzed azide–alkyne cycloaddition (CuAAC), the CuAIAC reaction has remained overlooked by the synthetic community for almost a decade. Since 2010, however, CuAIAC reaction started to emerge as a promising supplement to the well-known CuAAC reaction. The present review surveys primarily the literature on CuAIAC reaction since 2003. Beside this, azomethine imine–alkyne cycloadditions catalyzed by other metals, selected examples of metal-free reactions, and related [3+3] and [3+4] cycloadditions of azomethine imines are presented. All these experimental data indicate the viability of CuAIAC in organic synthesis and the applicability in ‘click’ chemistry.1 Introduction2 Reactions with Acyclic Azomethine Imines3 Reactions with C,N-Cyclic Azomethine Imines4 Reactions with N,N-Cyclic Azomethine Imines5 Reactions with C,N,N-Cyclic Azomethine Imines6 The Mechanism of the CuAIAC Reaction7 Conclusions and Outlook

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“…Soon after, the same catalyst was also employed in kinetic resolution of azomethine imines by [3+2] cycloaddition [ 14 ]. Besides Cu(I)-, also Ag(I)- and Cu(II)-catalysts are amenable in cycloadditions to acetylenes [ 11 , 15 ]. In the reactions of olefins, however, asymmetric organocatalysts comprise the leading approach, although examples of metal-catalysis have also been reported [ 8 , 11 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Non-Racemic Pyrazolines and Pyrazolidines by [3+2] Cycloadditions of Azomethine Imines

et al. 2017

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Asymmetric [3+2] cycloadditions of azomethine imines comprise a useful synthetic tool for the construction of pyrazole derivatives with a variable degree of saturation and up to three stereogenic centers. As analogues of pyrrolidines and imidazolidines that are abundant among natural products, pyrazoline and pyrazolidine derivatives represent attractive synthetic targets due to their extensive applications in the chemical and medicinal industries. Following the increased understanding of the mechanistic aspect of metal-catalyzed and organocatalyzed [3+2] cycloadditions of 1,3-dipoles gained over recent years, significant strides have been taken to design and develop new protocols that proceed efficiently under mild synthetic conditions and duly benefit from superior functional group tolerance and selectivity. In this review, we represent the current state of the art in this field and detailed methods for the synthesis of non-racemic pyrazolines and pyrazolidines via [3+2] metal and organocatalyzed transformations reported since the seminal work of Kobayashi et al. and Fu et al. in 2002 and 2003 up to the end of year 2017.

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Combinatorial Synthesis of Acacen-Type Ligands and Their Coordination Compounds

Cited by 10 publications

References 48 publications

Synthesis of Enaminone‐Pd(II) Complexes and Their Application in Catalysing Aqueous Suzuki‐Miyaura Cross Coupling Reaction

Synthesis of Enaminone‐Pd(II) Complexes and Their Application in Catalysing Aqueous Suzuki‐Miyaura Cross Coupling Reaction

Copper-Catalyzed Azomethine Imine–Alkyne Cycloadditions (CuAIAC)

Synthesis of Non-Racemic Pyrazolines and Pyrazolidines by [3+2] Cycloadditions of Azomethine Imines

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