期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2021, 期 34, 页码 4777-4789出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202100698
关键词
Catalytic green solvents; Click chemistry; Copper-catalyzed azide-alkyne cycloadditions; Density functional calculations; Natural deep eutectic solvents
Natural deep eutectic solvents (NADESs) were used as reaction media in copper-catalyzed azide-alkyne cycloaddition reactions (CuAAc) in this study, showing high efficiency and excellent yields. NADESs demonstrated strong reducing capabilities without the need for added bases and stabilized copper catalytic intermediates through hydrogen bonding.
The click cycloaddition of azides to alkynes affording 1,2,3-triazoles is a widely used and effective chemical transformation, applied to obtain relevant products in medicine, biology, and materials science. In this work, a set of natural deep eutectic solvents (NADESs) has been investigated in the copper-catalyzed azide-alkyne cycloaddition reactions (CuAAc) as green and catalytic reaction media. The use of these innovative solvents has been shown to improve the reaction effectiveness, giving excellent yields. NADESs proved to be active in their reducing capabilities in several cases and for the absence of added bases in all the performed reactions: DFT calculations demonstrated in fact the involvement of H-bonds between DESs and alkynes, as well as stabilization of copper catalytic intermediates. The green experimental conditions, the absence of a base, the low temperatures, the lowering of reagent amounts, and the possibility of recycling of the solvents, outline the great potential of NADESs for CuAAc.
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