Metals as “Click” catalysts for alkyne-azide cycloaddition reactions: An overview

Kalra, Pooja; Kaur, Rupinder; Singh, Gurleen; Singh, Harminder; Singh, Gurjaspreet; Pawan, -; Kaur, Gurpreet; Singh, Jandeep

doi:10.1016/j.jorganchem.2021.121846

Cited by 42 publications

(27 citation statements)

References 144 publications

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“…Despite the fact that a variety of fluorophores is known [ 12 ], in the last decade, chemists and biologists have been interested in new fluorescent compounds based on 1,2,3-triazole [ 13 ]. Triazole-based fluorophores can be easily synthesized using a “click chemistry” approach, i.e., Cu-catalyzed azide–alkyne cycloaddition (CuAAC) [ 14 , 15 ]. Moreover, the fluorescent properties of triazoles are strongly dependent on the nature of the substituents attached to the N1, C4, and C5 positions, which can be varied easily through CuAAC.…”

Section: Introductionmentioning

confidence: 99%

4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications

et al. 2022

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Cu-catalyzed 1,3-dipolar cycloaddition of ethyl 2-azidoacetate to iodobuta-1,3-diynes and subsequent Sonogashira cross-coupling were used to synthesize a large series of new triazole-based push–pull chromophores: 4,5-bis(arylethynyl)-1H-1,2,3-triazoles. The study of their optical properties revealed that all molecules have fluorescence properties, the Stokes shift values of which exceed 150 nm. The fluorescent properties of triazoles are easily adjustable depending on the nature of the substituents attached to aryl rings of the arylethynyl moieties at the C4 and C5 atoms of the triazole core. The possibility of 4,5-bis(arylethynyl)-1,2,3-triazoles’ application for labeling was demonstrated using proteins and the HEK293 cell line. The results of an MTT test on two distinct cell lines, HEK293 and HeLa, revealed the low cytotoxicity of 4,5-bis(arylethynyl)triazoles, which makes them promising fluorescent tags for labeling and tracking biomolecules.

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Section: Introductionmentioning

confidence: 99%

4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications

et al. 2022

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“…The term "click chemistry" was coined by Sharpless and co-workers in 2002; 78 to be considered as a "click" reaction, certain characteristics must be fulfilled: (1) easily accessible reagents, (2) no need of a solvent or a solvent that is benign (e.g., water), (3) insensitive to oxygen, (4) high yield, (5) stereospecific products, and ( 6) easily removable by-products without the need of chromatographic techniques. 79 These features are attributed to the high thermodynamic driving force ( 20 kcal mol -1 ), promoting the reaction to reach the completion with high selectivity. 78 Four major types of click reactions have been identified, including cycloaddition (Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of azide-alkynes); nucleophilic ring-openings (openings of strained heterocyclic electrophiles); non-aldol carbonyl chemistry (hydrazone/oxime ether formation, and amide/isourea formation); and multiple carbon bond additions (the formation of different three-member rings, and Michael addition).…”

Section: Click Reaction On Surfacementioning

confidence: 99%

“…Before the discovery of Cu(I) catalyst by Sharpless and Meldal, the reaction was depending on elevated temperature and prolonged reaction duration, which results in a mixture of 1,4and 1,5-triazole regio-isomers. 79 In comparison, other metal catalysts employed in azidealkyne cycloaddition, e.g., like Zn(II), 81,82 and Ru(II), 83,84 require either challenging reaction conditions or further purification of the products, besides the relatively low yield. As for the development of sensors and other molecular electronics, the efficient and convenient immobilization of specific molecules on surface is of practical importance.…”

Section: (A) (B)mentioning

confidence: 99%

“Click” Cucurbit[7]uril Hosts on Self-Assembled Monolayers: Quantitative Supramolecular Complexation with Ferrocene Guests

et al. 2022

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Cucurbit[7]uril (CB[7]), a symmetrical pumpkin-shaped molecule with an internal volume that can encapsulate guest molecules of complementary shape and size at a 1:1 ratio, has attracted tremendous attention in diverse fields. Particularly, the outstanding in-solution binding affinity (Kf  10 9 M -1 ) of the host-guest inclusion complexation between cucurbit[7]uril molecule host and ferrocene derivatives molecule guests (Fc@CB[7]) enables their potential applications as conjugation/immobilization motifs for constructing biosensors and other molecular devices. However, their interfacial host-guest complexation behaviour has been rarely studied, partially due to the limitation of current CB [7] surface immobilization strategies (suffering from either poor stability or time-consuming and inconvenient procedure). In this thesis, it was shown that the well-known copper(I)-catalyzed azide-alkyne cycloaddition "click" reaction (CuAAC) can be used to chemically attach alkyne-functionalized CB[7] onto an azide-terminated selfassembled monolayer (SAM) on gold. The reaction time has been reduced from several hours to 30 min compared to conventional methods (e.g., the olefin metathesis reaction or the thiol-ene "click" reaction). Thus prepared CB[7]-tethered SAMs enabled the determination of complexation properties of CB [7] towards various Fc derivatives (e.g., neutral, positively charged and negatively charged substituents) on the surface via conventional cyclic voltammetry measurements. Particularly, the derived complexation thermodynamics (Kf = (1.6 ± 0.3)  10 7 M -1 ) for ferrocenemethanol (FcMeOH), and kinetics data (ka = (2.6 ± 0.4)  10 3 M -1 s -1 , kd = (5.1 ± 0.3)  10 -5 s -1 ) confirms its strong interfacial host-guest binding with the surface-immobilized CB [7]. Moreover, the as-strong binding affinity of surface-bound CB[7] toward an anionic ferrocene derivative confirms the feasibility of employing Fc@CB[7] as the conjugation motif for immobilizing biological macromolecules (that are often negatively charged) to biochip surfaces.

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“…Proposed by Sharpless in the past decade, click chemistry is a class of chemical reactions well-known because of its full advantages of being effective, reliable and selective and its high yields with little or no byproducts [ 28 , 29 , 30 ]. One of the most popular reactions within the click chemistry philosophy is the Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction between azide and terminal alkyne groups, which has received increasing attention because of its simple and powerful modular synthesis approach [ 30 , 31 , 32 ]. Moreover, there have been some reports about the combination of the click reaction and NPs for further applications [ 33 , 34 , 35 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Xylan-Click-Quaternized Chitosan via Click Chemistry and Its Application in the Preparation of Nanometal Materials

et al. 2022

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For the high-valued utilization of hemicelluloses and for realizing the controllable synthesis of NPs, this paper’s aim is to combine xylan, chitosan and nanometal materials at the same time. In this research study, firstly, propargyl xylan was synthesized via nucleophilic substitution reaction between xylan and propargyl bromide in NaOH solution. On the other hand, a tosyl group was introduced onto the 6th position of synthesized quaternized chitosan (QCS), and the azide group replaced the tosyl group to obtain 6-amido-QCS (QCS-N3). The synthesis conditions of the above reactions were optimized. Subsequently, the novel xylan-click-QCS polymer was obtained via click reaction between terminal alkyne groups on the xylan chains and azide groups on QCS. Then, AgNPs and AuNPs were synthesized by adopting the xylan-click-QCS polymer as the reducing and stabilizing agent, and the reaction conditions were optimized to obtain well-dispersed and highly stable nanoparticles. There were two kinds of Ag nanomaterials, with diameters of 10~20 nm and 2~5 nm, respectively, indicating the formation of Ag nanoclusters, except for Ag nanoparticles, in this reaction. The diameter of the synthesized AuNPs was 20~30 nm, which possessed a more uniform size distribution. The Ag nanoclusters with a smaller size (2~5 nm) could inhibit MCF-7 cell proliferation effectively, indicating their application potential in cancer therapy. The study gives a new approach to the high-value utilization of biopolymers.

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Metals as “Click” catalysts for alkyne-azide cycloaddition reactions: An overview

Cited by 42 publications

References 144 publications

4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications

4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications

“Click” Cucurbit[7]uril Hosts on Self-Assembled Monolayers: Quantitative Supramolecular Complexation with Ferrocene Guests

Synthesis of Xylan-Click-Quaternized Chitosan via Click Chemistry and Its Application in the Preparation of Nanometal Materials

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