Cu Nano particles immobilized on silk‐fibroin as a green and biodegradable catalyst for copper catalyzed azide‐terminal, internal alkynes cycloaddition

Abstract

Copper immobilized on silk fibroin was successfully prepared and fully characterized using powder X-ray diffraction, scanning electron microscopy-energydispersive X-ray spectroscopy, Fourier transform-infrared, CHN elemental analysis, and inductively coupled plasma-atomic emission spectroscopy. Catalytic activity of this catalyst was examined in the azide-alkyne cycloaddition reaction with internal and terminal alkynes at room temperature under mild conditions. The reusability of the heterogeneous supported Cu catalyst was examined four times without significant loss of catalytic activity.

Rejuvenating the [1, 2, 3]-triazolo [1,5-a]quinoxalin-4(5H)-one scaffold: Synthesis and derivatization in a sustainable guise and preliminary antimicrobial evaluation

“…The resulting azides were then engaged in the click reaction with dimethyl acetylene dicarboxylate as the alkyne, without the need of catalysts or halogenated solvents providing the corresponding dimethyl carboxylate triazoles ( 4a-i ) and avoiding the formation of previously described byproducts when using diethyl oxalacetate, ethyl benzoyl pyruvate and ethyl 2-furoyl pyruvate sodium salts. It is worth of note that for the generation of 1,4,5-trisubstituted 1,2,3-triazole moieties, only 2 references for the click reaction of 2-nitrophenyl azides and dimethyl acetylenedicarboxylate have been reported in literature, using copper nanoparticles immobilized on silk fibroin ( Mirzaei et al, 2021 ) or regular stirring and microwave irradiation in dichloromethane ( Souad et al, 2011 ). A relevant part of this project was then devoted to the exploration of different eco-compatible reaction conditions, using 2-nitrophenyl azide and dimethyl acetylene dicarboxylate as the starting materials in combination with different solvents, ionic liquids and catalysts, and also through the use of microwave and ultrasound bath ( Table 1 ).…”

A New Insight Into The Huisgen Reaction: Heterogeneous Copper Catalyzed Azide‐Alkyne Cycloaddition for the Synthesis of 1,4‐Disubstituted Triazole (From 2018–2023)

“…Mirzaei and team reported a novel copper nanoparticle immobilized on silk fibroin (Cu/Fibroin). They have developed a novel catalytic method for the synthesis of 1,2,3‐triazoles from aryl azides and both terminal and internal alkynes [106] . Fourier transform‐infrared analysis shows the characteristics bands and indicate the metal‐fibroin interaction.…”

“…They have developed a novel catalytic method for the synthesis of 1,2,3-triazoles from aryl azides and both terminal and internal alkynes. [106] Fourier transform-infrared analysis shows the characteristics bands and indicate the metal-fibroin interaction. X-ray diffraction (XRD) analysis identifies the crystalline structure of Cu NPs (Cu/Fib.)…”

Palladium Supported on Silk Fibroin for Suzuki–Miyaura Cross‐Coupling Reactions

“…[ 20 ] After over 40 years, Pd/SF has been rediscovered as versatile catalyst for chemoselective hydrogenation of alkenes, alkynes, azides and nitro groups, [ 21 ] and more recently for Heck reactions. [ 22 ] However, the true potential of Pd catalysts supported on SF fibers is still almost unexplored, especially in cross‐coupling chemistry.…”