Ligand Synthesis Catalyst and Complex Metal Ion: Multicomponent Synthesis of 1,3-Bis(4-phenyl-[1,2,3]triazol-1-yl)-propan-2-ol Copper(I) Complex and Application in Copper-Catalyzed Alkyne-Azide Cycloaddition

Abstract

A new bistriazole copper complex was synthesized by direct treatment of an alkyne, an azide, and CuI as copper salt throughin situligand formation under a multicomponent reaction process. This complex was analyzed by XPS, TGA, DSC, and SEM techniques and revealed a triangular-shaped morphology, high thermal stability, and catalytic power in CuAAC reactions, requiring only 2.5% mol catalyst to afford 1,2,3-triazoles in good yields which can be reused at least for 4 cycles.

Synthesis of 1,2,3-Triazoles from Alkyne-Azide Cycloaddition Catalyzed by a Bio-Reduced Alkynylcopper (I) Complex

“…Thus, the successively addition of Fehling A and B solutions to a mixture glucose-phenylacetylene produced a characteristic yellow precipitate which was identified as phenylethynylcopper (I) 1 presenting the same physical data described in literature (Scheme 1) [12,13]. In addition, XPS analysis of compound 1 displays a signal 2p 3/2 at 935 eV corresponding to a copper species with oxidation number (I) in agreement to previous reports (Figure 1) [10,14], whereas a signal at 533.8 eV (spectrum b, Figure 1) suggests a Cu-C interaction [15,16]; moreover, C 1s bond energy at 285.8 eV assigned to aromatic carbons confirmed the formation of copper (I) phenylacetylide 1 which was used in following steps. The reaction between 1-ethynylcyclohexanol 2 and benzylazide 3 was used as model to evaluate the catalytic activity of phenylacetylide 1 (Scheme 2).…”

“…In conjunction with other research, we observed in situ formation of 1,2,3-triazole copper complexes by a straightforward mixing of alkyne, azide and a copper (I) salt [10]. From these studies, we detected the formation of a copper acetylide and we decided to investigate in detail this process aimed to prepare efficient catalysts for the synthesis of 1,2,3-triazoles through CuAAC reactions.…”

Tetrazol-Cu(i) immobilized on nickel ferrite catalyzed green synthesis of indenopyridopyrimidine derivatives in aqueous media

“…The use of copper complexes in various chemical reactions, such as alkyne–azide cycloaddition, 33 hydroboration reactions, 34 allylic alkylation reactions, 35 direct addition of terminal alkynes to imines, 36 and β-boration of α,β-unsaturated esters, 37 has led us to the use of these compositions as a catalyst in this reaction.…”