Journal
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
Volume 14, Issue 2, Pages 509-519Publisher
SPRINGER
DOI: 10.1007/s13738-016-0999-3
Keywords
Click' cycloaddition; Heterogeneous catalyst; beta-azido alcohols; Terminal alkynes; beta-hydroxytriazolylalkyl
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A facile and simple protocol for the 'Click' cycloaddition of organic azides with terminal alkynes catalyzed by immobilized [Cu(cdsalMeen)] on silica as a new and convenient heterogeneous catalyst is described. In this synthetic methodology, [Cu(cdsalMeen)]-SiO2 catalyzes 1,3-dipolar Huisgen cycloaddition of different functionalized beta-azido alcohols and alkynes in the presence of ascorbic acid and a solution of THF/H2O (2:1, V/V) at room temperature. Good to excellent yields of beta-hydroxytriazolylalkyl derivatives were afforded using [Cu(cdsalMeen)]-SiO2. Immobilization of [Cu(cdsalMeen)] on silica was approved as a chemically and thermally stable catalyst that can be reused for many consecutive trials without a significant decline in its reactivity. [GRAPHICS] .
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