A straightforward and sustainable synthesis of 1,4-disubstituted 1,2,3-triazoles via visible-light-promoted copper-catalyzed azide–alkyne cycloaddition (CuAAC)

Abstract

A simple and green synthesis of 1,4-disubstituted 1,2,3-triazoles through the effective reduction of copper(II) assisted by organic dyes and promoted by visible light was developed. This reaction was performed under very mild conditions, using water as solvent, under a non-inert atmosphere, with low catalyst precursor loading, and in the absence of any additive. Copper and solvent recycling was successfully achieved at least three times without loss of efficiency. In addition, a safer one-step one-pot procedure was designed with very good yield.

CoFe2O4/Cu(OH)2 magnetic nanocomposite: an efficient and reusable heterogeneous catalyst for one-pot synthesis of β-hydroxy-1,4-disubstituted-1,2,3-triazoles from epoxides

“…13 The Huisgen 1,3-dipolar cycloaddition of alkynes and organic azides has been developed as the principal method for synthesis of 1,2,3-triazoles. [14][15][16][17][18][19][20][21][22] Recently, multicomponent onepot synthesis of b-hydroxy-1,2,3-triazoles has been carried out through in situ click reaction of azides, alkynes and epoxides in the presence of heterogeneous copper catalysts such as carbon supported copper nanoparticles, 23,24 porphyrinatocopper nanoparticles, 25 CuSO 4 $5H 2 O/sodium ascorbate, 26 copper(I)-zeolite, 27 Cu[N 2 ,N 6 -bis(2-hydroxyphenyl)pyridine-2,6-dicarboxamidate]/ ascorbic acid, 28 copper ferrite nanoparticles, 29 copper(I)@phosphorated SiO 2 , 30 Cu(OAc) 2 $H 2 O, 31 (Cu/Cu 2 O) nanoparticles, 32 Cu(II)-azide complexes, 33 Cu(II)-DA@nano AlPO 4 , 34 1,4-dihydroxyanthraquinone-copper(II) nanoparticles immobilized on silica gel, 35 4 0 -phenyl-2,2 0 :6 0 ,2 00 -terpyridine copper(II) complex immobilized on activated multiwalled carbon nanotubes, 36 CuI 37 and NiFe 2 O 4 -glutamate-Cu. 38 Ramachary-Bressy-Wang cycloaddition of enolate intermediates and organic azides is the other basic method for one-pot preparation of 1,4-disubstituted-1,2,3-triazoles.…”

Pyrene‐Tagged Chloro Oximes as Ambient‐Light‐Accelerated Ligation Agents

“…For example, pyrene attached to azirines, tetrazoles, and acyl sulfides can lead to highly reactive 1,3‐dipoles or dienophiles when irradiated with wavelengths exceeding 400 nm. Other methods for efficient visible light induced ligation reactions include the use of photocatalysts for thiol‐ene, and thiol‐yne additions, or copper(I)‐catalysed cycloaddition of azides and alkynes ,…”

“…Other methods for efficient visible light induced ligation reactions include the use of photocatalysts for thiol-ene [16,17] and thiol-yne additions, [18] or copper(I)-catalysed cycloaddition of azides and alkynes. [19,20] On the other hand, 4,5-dihydroisoxazoles (isoxazolines) and isoxazoles are important compounds in the field of pharmaceutical and therapeutic applications due to their wide range of bioactivity, [21][22][23] and in the synthesis of natural products as they can be readily converted into various substrates, [24] including amino alcohols, [25] hydroxyl ketones, [26] and themselves. [27] These heterocycles are readily available through cycloaddition of nitrile oxides to alkenes and alkynes, respectively.…”

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

“…In contrast, they proved efficient for the three-component synthesis of 1,4-disubstituted 1,2,3-triazoles starting from terminal alkynes, NaN3 and organic halides (R-X). Milder conditions were required using CuCl2 as catalyst in combination with an organic photosensitizer (eosin Y disodium salt (EY)) and green LED irradiation (Scheme 7c) [66]. The CuCl2/EY photocatalytic system enabled the isolation of a broad family of 1,4-disubstituted 1,2,3-triazoles in moderate to excellent yields (49-100%) and the aforementioned catalytic system was recycled up to three consecutive runs [66].…”