13148-78-2Relevant articles and documents
Selectivity in an encapsulated cycloaddition reaction
Chen, Jian,Rebek Jr., Julius
, p. 327 - 329 (2002)
(Equation Presented) A 1,3-dipolar cycloaddition takes place within a reversibly formed, self-assembled capsule. The reaction proceeds through an unsymmetrically loaded encapsulation complex with absolute regioselectivity.
Copper(I)-catalyzed azide-alkyne cycloadditions in microflow: Catalyst activity, high-T operation, and an integrated continuous copper scavenging unit
Varas, Alvaro Carlos,Noel, Timothy,Wang, Qi,Hessel, Volker
, p. 1703 - 1707,5 (2012)
Avoiding the coppers: A continuous-flow synthesis for the Cu I-catalyzed azide-alkyne cycloaddition reaction using [Cu(phenanthroline)(PPh3)2]NO3 as a homogeneous catalyst is developed (up to 92 % isolated yield). Elevated temperatures allow achieving full conversions and using lower catalyst loadings. Residual copper in the triazole compound is efficiently removed via an inline extraction process, employing aqueous EDTA as a copper scavenger. Copyright
Copper-Catalyzed Four-Component Cascade Reaction for the Construction of Triazoles Bearing β-Hydroxy Chalcogenides
Wang, Xiang-Xiang,Sun, Bo-Xun,Zhao, Zhi-Wei,Chen, Xin,Xia, Wen-Jin,Shen, Yuehai,Li, Ya-Min
supporting information, p. 165 - 171 (2021/10/19)
A copper-catalyzed four-component cascade reaction for the preparation of triazoles bearing β-hydroxy chalcogenides from terminal alkynes, azides, epoxides, and Se/K2S is reported. The present reaction proceeds under mild conditions, and exhibits a good functional group compatibility. A possible mechanism is proposed. (Figure presented.).
Immobilization of vitamin B1 on the magnetic dialdehyde starch as an efficient carbene-type support for the copper complexation and its catalytic activity examination
Abbaspour, M.,Mohammadi Ziarani, G.,Rafiee, F.
, (2021/11/16)
Since the starch biopolymer is an available and inexpensive matrix with modifiable functionality and stabilization capability for metal ions, in this report, we oxidized it to dialdehyde form for the further functionalization with vitamin B1 as a green σ-donor and π-acceptor carbene type ligand. Immobilization of vitamin B1 on this biopolymer was done through imine bond formation between NH2 groups of aminopyrimidine segment of vitamin B1 and aldehyde functional groups of starch oxide. Thiazolium heterocycle part in this biomolecule provided a carbene type precursor for the metal complexation. After the magnetization process by using of Fe3O4 nanoparticles that lead to quick and facile magnetic separation and metal catalyst recycling, copper ions immobilized on the magnetic support (5.9 wt% Cu, 0.93 mmol/g). The prepared copper N-heterocyclic carbene complex (Fe3O4@DAS@VB1@CuCl nanocomposite) was characterized by FT-IR, SEM, EDX, XRD, VSM, TGA and ICP-OES analysis and then its catalytic activity investigated in azidonation of arylboronic acids and also one-pot coupling reaction of the synthesized aryl azides with phenylacetylene. 1,4-Diaryl 1,2,3-triazoles were obtained in excellent yields (≥90%) at proper reaction times (30–200 min). The magnetic catalyst was recovered by a magnetic field and reused in azidation reaction up to 7 cycle.
Synthetic access to ring-expanded N-heterocyclic carbene (Re-NHC) copper complexes and their performance in click chemistry
Bouchet, Damien,Cazin, Catherine S. J.,Hall, Jonathan W.,Mahon, Mary F.,Whittlesey, Michael K.
, p. 1252 - 1261 (2021/05/29)
The facile syntheses of ring-expanded N-heterocyclic carbene (RE-NHC) copper(I) halide complexes are reported. The method makes use of a weak inorganic base in a green solvent. The reaction times can be greatly reduced by use of this weak-base route under microwave irradiation. The easy access to these complexes permits an evaluation of the catalytic activity and reaction profiling of [Cu(RE-NHC)X] complexes in the Huisgen 1,3-cycloaddition reaction.