Biosourced cyclosophoraose-driven acceleration of click reaction in H2O

• Published in: Journal of industrial and engineering chemistry (Seoul, Korea) Vol. 59; pp. 372 - 376
• Main Authors: Cho, Eunae, Jeong, Daham, Dindulkar, Someshwar D., Jung, Seunho
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 25.03.2018; 한국공업화학회
• Subjects: 1,2,3-Triazoles; Aqueous medium; Click reaction; Cyclosophoraose; Huisgen cycloaddition; 화학공학; 1,2,3-Triazoles; Click reaction; Cyclosophoraose; Aqueous medium; Huisgen cycloaddition
• ISSN: 1226-086X; 1876-794X
• DOI: 10.1016/j.jiec.2017.10.045

[Display omitted] •A facile synthetic strategy of 1,4-disubstituted-1,2,3-triazoles in H2O is reported.•Cyclosophoraoses purified from Rhizobium species promoted the click reaction of azide and alkyne in water.•The supramolecular catalytic system provides a simple, workup-free, and green catalytic platform for aqueous click reaction. Here, we report biosourced cyclosophoraose (CyS)-promoted click reaction of organic azides and alkynes in water, where CyS, rhizobial cyclic β-1,2 glucan molecules containing 17–23 glucoses, dramatically decreased the reaction time from hours to minutes via the solubilization of aromatic alkynes. This catalytic system was successfully applied to the copper-mediated Huisgen 1,3-dipolar cycloaddition reaction using in situ-generated azide. The developed strategy yielded 1,4-disubstituted-1,2,3-triazoles after a short reaction time without bases from a room-temperature aqueous medium, and the products were purified simply by precipitation without requiring further column purifications.