[3 + 2] Cycloaddition of acetylenes with azides to give 1,4-disubstituted 1,2,3-triazoles in a modular flow reactor

Smith, Christopher; Baxendale, Ian R.; Lanners, Steve; Hayward, John; Smith, Stephen C.; Ley, Steven V.

doi:10.1039/b702995k

Cited by 124 publications

(65 citation statements)

References 22 publications

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“…[17] In 2005, it was discovered that copper metal turnings or powder, in stoichiometric quantity, could be a source of the catalytic species involved in the title click reaction. [18] Since 76 then, the use of copper nanoparticles (CuNPs), instead of bulk copper, has been increasingly explored to reduce both the catalyst loading and the reaction times.…”

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confidence: 99%

Unsupported Copper Nanoparticles in the 1,3‐Dipolar Cycloaddition of Terminal Alkynes and Azides

et al. 2010

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Readily prepared copper nanoparticles were found to catalyse the 1,3‐dipolar cycloaddition of azides and alkynes up to rates comparable to those of microwave chemistry. Both the preparation of the nanoparticles and the click reaction are carried out under mild conditions, in short reaction times and in the absence of any stabilising additive or ligand. A variety of 1,2,3‐triazoles were prepared in excellent yields. A reaction mechanism was postulated on the basis of different reactivity studies and deuteration experiments. Copper(I) acetylides were demonstrated to be the real intermediate species.

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confidence: 99%

Unsupported Copper Nanoparticles in the 1,3‐Dipolar Cycloaddition of Terminal Alkynes and Azides

et al. 2010

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“…In addition, Smith et al described the successful removal of CuI and excess azide using a modular flow reactor system comprised of three continuous columns containing different polymer resins. 11 Herein, we report a very simple and expedient method for the rapid preparation of 1,4-disubstituted 1,2,3-triazole using scavenger resins to remove unreacted azide/alkyne after the solution-phase click reaction. Subsequently, copper catalyst is also removed by simple filtration.…”

Section: Introductionmentioning

confidence: 99%

Azide/Alkyne Resins for Quick Preparation of 1,4-Disubstituted 1,2,3-Triazoles

Sirion¹,

Lee²,

Bae³

et al. 2010

Bulletin of the Korean Chemical Society

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An efficient method for the preparation of 1,4-disubstituted 1,2,3-triazole compounds is described using polymeric quaternary ammonium salts having azide or alkyne functionality to remove unreacted excess starting molecules (azide/alkyne). Copper metal could easily be removed by simple filtration with a short Na2SO4/silica cartridge, affording highly regioselective products in high yield and excellent purity without the need for work-up, extraction and chromatographic purification.

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“…These include treatment of peptide-containing dendrimers with Na 2 S, 29 multiple extractions with solutions of EDTA, 30 dialysis against EDTA solution 31 and the use of copper chelating resins. 32 Various flow techniques for elimination of copper traces have been developed as well. 30,33 Careful control of copper content is necessitated by aspects such as limits on heavy metals in pharmaceutically active compounds, 30 product stability 34 and inhibition of enzymes by copper ions.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 1,2,3-triazole-linked galactohybrids and their inhibitory activities on galectins

Mackeviča¹,

Ostrovskis²,

Leffler³

et al. 2014

Arkivoc

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Here a synthesis of novel galactose-1,2,3-triazole conjugates is described. The title compounds were obtained from 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-galactofuranose via a copper catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction. It was demonstrated that the title compounds in their isopropylidene-protected form tend to chelate copper. The copper content can be diminished to 10 ppm by successive treatment with EDTA and Na 2 S followed by chromatographic purification. Acidic hydrolysis of the acetonide protecting groups provided water soluble galactohybrids that were tested for their affinity towards galectin-1 and galectin-3. The trimeric galactohybrid exhibited a 160-fold preference for galectin-3 binding with K d 50 μM. One of the obtained disaccharides was characterized by X-ray analysis.

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[3 + 2] Cycloaddition of acetylenes with azides to give 1,4-disubstituted 1,2,3-triazoles in a modular flow reactor

Abstract: The cycloaddition of acetylenes with azides to give the corresponding 1,4-disubstituted 1,2,3-triazoles is reported using immobilised reagents and scavengers in pre-packed glass tubes in a modular flow reactor.

Cited by 124 publications

References 22 publications

Unsupported Copper Nanoparticles in the 1,3‐Dipolar Cycloaddition of Terminal Alkynes and Azides

Unsupported Copper Nanoparticles in the 1,3‐Dipolar Cycloaddition of Terminal Alkynes and Azides

Azide/Alkyne Resins for Quick Preparation of 1,4-Disubstituted 1,2,3-Triazoles

Synthesis of 1,2,3-triazole-linked galactohybrids and their inhibitory activities on galectins

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