Novel Cu() acidic deep eutectic solvent as an efficient and green multifunctional catalytic solvent system in base-free conditions to synthesize 1,4-disubstituted 1,2,3-triazoles

A novel green Cu( ii )-acidic deep eutectic solvent (Cu( ii )-ADES) bearing copper salt, choline chloride, and gallic acid ([ChCl] 4 [2GA-Cu( ii )]) was synthesized and thoroughly specified by physicochemical approaches such as FT-IR, EDX, XRD, Mapping, ICP, and UV-Vis analyses and physicochemical p...

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Bibliographic Details
Published in:RSC advances 2023-12, Vol.13 (51), p.3643-36415
Main Authors: Bagherzadeh, Nastaran, Amiri, Mohammad, Sardarian, Ali Reza
Format: Article
Language:English
Subjects:
Alkynes
Amines
Caprolactam
Chemical reactions
Chemistry
Choline
Copper
Functional groups
Gallic acid
Nitrogen dioxide
Reducing agents
Sodium azides
Solvents
Substrates
Triazoles
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Summary:A novel green Cu( ii )-acidic deep eutectic solvent (Cu( ii )-ADES) bearing copper salt, choline chloride, and gallic acid ([ChCl] 4 [2GA-Cu( ii )]) was synthesized and thoroughly specified by physicochemical approaches such as FT-IR, EDX, XRD, Mapping, ICP, and UV-Vis analyses and physicochemical properties. After the detection of authentic data, the central composite design (CCD) was utilized to accomplish the pertaining tests and develop the optimum condition, and, in the following, [ChCl] 4 [2GA-Cu( ii )] was applied as a green multifunctional catalytic solvent system in reducing agent-free and base-free condition for the three-component click reaction from sodium azide, alkyl, allyl, ester, and benzyl halide, and terminal alkyne made from amines and caprolactam as a cyclic amide to furnish a successful new library of 1,4-disubstituted 1,2,3-triazoles with a yield of up to 98%. The Cu( ii )-ADES is stable and can comfortably be recovered and reused without a considerable decline in its acting for seven cycles. This triazole synthesizing methodology is distinguished via its atom economy, operational facility, short reaction times, diverse substrate scope, and high performance for large-scale synthesis of the desired products including: -CN and -NO 2 as efficient functional groups. A novel Cu( ii )-acidic deep eutectic solvent was synthesized by the eco-friendly strategy and applied as multifunctional catalytic solvent system to furnish high yield of 1,2,3-triazoles in reducing agent- and base-free condition via CuAAC reaction.
ISSN:2046-2069
2046-2069
DOI:10.1039/d3ra06570g