Green Methodologies for Copper(I)-Catalyzed Azide-Alkyne Cycloadditions: A Comparative Study
Marissa Trujillo,Clayton Hull-Crew,Andrew Outlaw,Kevin Stewart,Loren J. Taylor,Laura George,Allison Duensing,Breanna Tracey,Allen M. Schoffstall +8 more
TL;DR: The results lead to the conclusion that the microwave method should be strongly considered for CuAAC syntheses.
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Abstract: Successful copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions may be achieved by several methods. In this paper, four synthetic protocols were performed for direct comparison of time required for the synthesis, yield, and purity of the 1H-1,2,3-triazole products. The methods with Cu(I) catalysts were conventional, microwave heating, solvent-free, and a method using glycerol solvent. The compounds synthesized in this paper were known non-fluorinated triazoles and new fluorinated triazoles. The results lead to the conclusion that the microwave method should be strongly considered for CuAAC syntheses.
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Citations
Recent Progress of Cu-Catalyzed Azide-Alkyne Cycloaddition Reactions (CuAAC) in Sustainable Solvents: Glycerol, Deep Eutectic Solvents, and Aqueous Media
TL;DR: This mini-review presents a general overview of the progress achieved during the last decade on the amalgamation of CuAAC processes (copper-catalyzed azide-alkyne cycloaddition) with the employment of sustainable solvents as reaction media to fulfil several important principles of green chemistry.
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Synthesis, Characterisation and Crystal structure of a New Cu(II)-carboxamide Complex and CuO nanoparticles as New Catalysts in the CuAAC reaction and Investigation of their Antibacterial activity
Mahsa Kiani,Mojtaba Bagherzadeh,Soraia Meghdadi,Farzaneh Fadaei-Tirani,Maryam Babaie,Kurt Schenk-Joß +5 more
TL;DR: The bidentate carboxamide ligand N-(thiazole-2-yl) picolinamide (LH) was synthesized in the environmentally friendly ionic liquid TBAB, and the five-coordinated CuII-complex, [Cu(L)2(H2O)].CHCl3 as discussed by the authors has been synthesized from LH and copper(II)acetate.
17
Thymol as an Interesting Building Block for Promising Fungicides against Fusarium solani .
Mariana Alves Eloy,Rayssa Ribeiro,Leandra Martins Meireles,Thiago Antonio de Sousa Cutrim,Carla Santana Francisco,Clara L. Javarini,Warley de Souza Borges,Adilson Vidal Costa,Vagner Tebaldi de Queiroz,Rodrigo Scherer,Valdemar Lacerda,Pedro Alves Bezerra Morais +11 more
TL;DR: In this article, Williamson synthesis and copper-catalyzed azide-alkyne cycloaddition (CuAAC) approaches were used to synthesize 15 new triazolic thymol derivatives.
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Alkynyl‐ or Azido‐Functionalized 1,2,3‐Triazoles: Selective MonoCuAAC Promoted by Physical Factors
Maxim A. Topchiy,Maxim A. Topchiy,Alexandra A. Ageshina,Gleb A. Chesnokov,Grigorii K. Sterligov,Grigorii K. Sterligov,Sergey A. Rzhevskiy,Pavel S. Gribanov,Pavel S. Gribanov,Sergey N. Osipov,Mikhail S. Nechaev,Mikhail S. Nechaev,Andrey F. Asachenko,Andrey F. Asachenko +13 more
- 05 Jul 2019
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N-Heterocyclic Imine Supported Bimetallic Cu(II) Catalyst for Azide-alkyne cycloaddition: Solvent-free, Reductant free, ppm level catalysis to access 1,4-disubstituted triazoles.
S. Revathi,Tapas Ghatak +1 more
TL;DR: In this paper , a unique bimetallic paddle wheel copper (II) complex with the molecular formula [Cu2C42H54N6O8] was presented, which excels as a catalytic system in Parts-per-million level (ppm) loading for the azide-alkene 'click' reaction under solvent-free conditions.
6
References
Glycerol: a biorenewable solvent for base-free Cu(I)-catalyzed 1,3-dipolar cycloaddition of azides with terminal and 1-iodoalkynes. Highly efficient transformations and catalyst recycling
TL;DR: The combination of CuI and glycerol exhibits a versatile and high catalytic activity in the Huisgen cycloaddition of azides and terminal or 1-iodoalkynes under standard bench experimental conditions providing a pivotal contribution to Green Chemistry.
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TL;DR: The triazole synthesis results indicated that the lignin nanosphere-supported Cu2O catalyst had a high catalytic performance with 99% yield under solvent-free conditions and could be recycled for four times without significantly losing its catalytic activity.
Synthesis of magnetically separable catalyst Cu-ACP-Am-Fe3O4@SiO2 for Huisgen 1,3-dipolar cycloaddition
Sandip P. Vibhute,Pradeep M. Mhaldar,Suyog N. Korade,D.S. Gaikwad,R.V. Shejawal,Dattaprasad M. Pore +5 more
TL;DR: In this paper, the use of magnetically separable silica coated copper (Cu-ACP-Am-Fe3O4@SiO2) as a heterogeneous nanocatalyst for the Huisgen 1,3-dipolar cycloaddition reaction of alkyl or aryl halide, sodium azide and terminal alkyne, which provided a series of 1,4-disubstituted-1,2,3triazoles.
Synthesis, in vitro anticancer and antibacterial activities and in silico studies of new 4-substituted 1,2,3-triazole-coumarin hybrids.
Tatjana Gazivoda Kraljević,Anja Harej,Mirela Sedić,Sandra Kraljević Pavelić,Višnja Stepanić,Domagoj Drenjančević,Jasminka Talapko,Silvana Raić-Malić +7 more
TL;DR: It is indicated that coumarin-1,2,3-triazole could be used as the scaffold for structural optimization to develop more potent and selective anticancer agents and encourage further development of novel structurally related analogs of 33 as more effective 5-LO inhibitors.
Improved copper(I)-NHC catalytic efficiency on huisgen reaction by addition of aromatic nitrogen donors
Marie-Laure Teyssot,Aurélien Chevry,Mounir Traïkia,Malika El-Ghozzi,Daniel Avignant,Arnaud Gautier +5 more
TL;DR: Addition of aromatic amines such as phenanthroline and 4-DMAP (4-dimethylaminopyridine) increases copper(I)-catalyzed azide alkyne cycloaddition catalytic activity of [CuCl(SIMes] at a large range of temperatures in such a way that efficient catalysis can safely take place in hydro-alcoholic solvents.