Carboxymethylpullulan promoted Cu<sub>2</sub>O-catalyzed Huisgen-click reaction

Zhang, Weiwei; Ren, Baoqi; Jiang, Yuqin; Hu, Zhiguo

doi:10.1039/c4ra14813d

Cited by 13 publications

(5 citation statements)

References 57 publications

(11 reference statements)

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“…However, drawbacks are obvious, because of the unrecoverable and unreusable properties of small molecular organic acids. In order to overcome these problems, the authors latter on combined Cu 2 O and carboxymethylpullulan (CMP) for high-yield CuAAC reactions in water with a relatively short reaction times, and CMP still remained in water enabling easy recoverability and reusability [144]. Very recently, Cu 2 O supported on graphene nanosheet [145] served as recyclable and reusable heterogeneous catalyst with excellent catalytic activity for CuAAC.…”

Section: Cuaacmentioning

confidence: 99%

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Changlong

Ikhlef

Kahlal

et al. 2016

Coordination Chemistry Reviews

290

162

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Highlights-The review is focused on the mechanistic aspects and recent trends (since 2012) of the metal-catalyzed azide-alkyne cycloaddition (MAAC) so-called "click" reactions with catalysts based on various metals (Cu, Ru, Ag, Au, Ir, Ni, Zn, Ln), although Cu (I) catalysts are still the most used ones.-These MAAC reactions are by far the most common click reactions relevant to the "green chemistry" concept.-Mechanistic investigations are essential to reaction improvements and subsequent applications, and indeed as shown in this review the proposed mechanisms have been multiple during the last decade based on theoretical computations and experimental search of intermediates.-New trends are also presented here often representing both exciting approaches for various applications and new challenges for further mechanistic investigations.

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Section: Cuaacmentioning

confidence: 99%

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Changlong

Ikhlef

Kahlal

et al. 2016

Coordination Chemistry Reviews

290

162

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“…We invoked the mechanism based on the following considerations. (i) Much like CuO, it has been shown in several reports that Cu 2 O is also capable of catalyzing the click synthesis. − (ii) However, our optimization studies using Cu 2 O (Table , entry 10) have resulted only in trace amounts of the product. Incidentally, Michaud et al also observed the lack of catalytic activity for Cu 2 O toward click chemistry .…”

Section: Resultsmentioning

confidence: 95%

Practical Coprecipitation Approach for High-Aspect Ratio Cupric Oxide Nanoparticles: A Sustainable Catalytic Platform for Huisgen and Fluorogenic Click Chemistry

Sampath

Vadivelu

Raheem

et al. 2022

Ind. Eng. Chem. Res.

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Herein, we disclose a practical coprecipitation method, which grants access to cupric oxide nanoparticles in high aspect ratio together with comprehensive characterization (X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), field emission scanning electron microscopy (FESEM), high-resolution transmission electron microscopy (HR-TEM), dynamic light scattering (DLS), Brunauer–Emmett–Teller (BET), diffuse reflectance spectroscopy (DRS), Fourier transform infrared (FT-IR), and thermogravimetric analysis (TGA)). Based on the combined morphological, electronic, and structural features, the activity of the as-prepared CuO nanoparticles as a heterogeneous catalyst in Huisgen azide–alkyne cycloaddition was explored. This chemistry works well in water (green medium) by showing catalytic competence toward an array of structurally and electronically distinct alkynes/azides. The catalyst can be recovered and reused for six cycles without much significant loss in the morphology and nanocrystallinity and solution leach-out. The developed methodology can also be extended to the synthesis of fluorogenic clickates, which display attractive optoelectrochemical properties. High chemical yields, good atom economy, excellent regioselectivity, gram-scale synthesis, short reaction time, and no rigorous solvent extraction are some of the other noteworthy advantages from a sustainable chemistry perspective. Thus, the current approach is operationally benign with respect to not only catalyst preparation but also its subsequent applicability in click synthesis.

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“…Interestingly, the Cu(OAc) 2 to Cu 2 O-NPs conversion co-produced HOAc as by-product, that suggested the beneficial role of acidic media for the CuAAC reaction to proceed [73]. Built on these observations, the same group developed the fast and high-yielding 1,3-dipolar cycloaddition of organic azides with terminal alkynes catalyzed by Cu 2 O (0.5 mol%) in neat water using carboxymethylpullulans (CMP; 5 mol%) as a mild source of protons (see Scheme 9c) [74]. Remarkably, the Cu 2 O/CMP catalytic system was efficiently recycled up to 6 consecutives runs, and might be recycled six additional runs upon acidic treatment that reactivates the CMP co-catalyst.…”

Section: Cu-catalyzed 13-dipolar Cycloaddition Of Azides and Alkynes (Cuaac) In Watermentioning

confidence: 99%

Recent Progress of Cu-Catalyzed Azide-Alkyne Cycloaddition Reactions (CuAAC) in Sustainable Solvents: Glycerol, Deep Eutectic Solvents, and Aqueous Media

Nebra

García‐Álvarez

2020

Molecules

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This mini-review presents a general overview of the progress achieved during the last decade on the amalgamation of CuAAC processes (copper-catalyzed azide-alkyne cycloaddition) with the employment of sustainable solvents as reaction media. In most of the presented examples, the use of water, glycerol (Gly), or deep eutectic solvents (DESs) as non-conventional reaction media allowed not only to recycle the catalytic system (thus reducing the amount of the copper catalyst needed per mole of substrate), but also to achieve higher conversions and selectivities when compared with the reaction promoted in hazardous and volatile organic solvents (VOCs). Moreover, the use of the aforementioned green solvents also permits the improvement of the overall sustainability of the Cu-catalyzed 1,3-dipolar cycloaddition process, thus fulfilling several important principles of green chemistry.

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Carboxymethylpullulan promoted Cu₂O-catalyzed Huisgen-click reaction

Abstract: Cu2O/CMP has been developed as a highly efficient catalytic system for Huisgen-click reaction in water at 60 °C.

Cited by 13 publications

References 57 publications

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Practical Coprecipitation Approach for High-Aspect Ratio Cupric Oxide Nanoparticles: A Sustainable Catalytic Platform for Huisgen and Fluorogenic Click Chemistry

Recent Progress of Cu-Catalyzed Azide-Alkyne Cycloaddition Reactions (CuAAC) in Sustainable Solvents: Glycerol, Deep Eutectic Solvents, and Aqueous Media

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Carboxymethylpullulan promoted Cu2O-catalyzed Huisgen-click reaction

Abstract: Cu2O/CMP has been developed as a highly efficient catalytic system for Huisgen-click reaction in water at 60 °C.

Cited by 13 publications

References 57 publications

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Practical Coprecipitation Approach for High-Aspect Ratio Cupric Oxide Nanoparticles: A Sustainable Catalytic Platform for Huisgen and Fluorogenic Click Chemistry

Recent Progress of Cu-Catalyzed Azide-Alkyne Cycloaddition Reactions (CuAAC) in Sustainable Solvents: Glycerol, Deep Eutectic Solvents, and Aqueous Media

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Carboxymethylpullulan promoted Cu₂O-catalyzed Huisgen-click reaction