A Microwave-Assisted Click Chemistry Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via a Copper(I)-Catalyzed Three-Component Reaction

Abstract

A microwave-assisted three-component reaction was used to prepare a series of 1,4-disubstituted-1,2,3-triazoles from corresponding alkyl halides, sodium azide, and alkynes. This procedure eliminates the need to handle organic azides, as they are generated in situ, making this already powerful click process even more user-friendly and safe.

New routes to Cu(i)/Cu nanocatalysts for the multicomponent click synthesis of 1,2,3-triazoles

“…The reaction with activated benzyl (Bn) bromide 1 was found to be signicantly promoted by dispersions of both mono-and bimetallic catalysts without the need for high temperatures and using substantially lower loadings than have previously proved effective for such transformations (0.03 mol% metal vs. 1-10 mol% previously). [43][44][45][46][47][48][49][50][51] Accordingly, Cu (samples 1 and 2; entries 1 and 2 in Consistent with PVP-coated NPs demonstrating Cu(I) oxide formation (vide supra) there is a difference observed between catalyst reactivities under atmospheres of air or Ar. Hence, sample 4 gave rather lower yields of 3 when used under Ar (compare entries 5 and 6 with entries 3 and 4).…”

Well-defined copper(i) complexes for Click azide–alkyne cycloaddition reactions: one Click beyond

“…76 Even though such drastic conditions might not be required in most cases, 77 this approach still has a large leeway for improvement.…”

Facile and efficient sonochemical synthesis of 1,4-disubstituted 1,2,3-triazole derivatives catalyzed by CuI under mild conditions

“…Although organic azides are stable against most reaction conditions, compounds of low molecular weight or those containing several azides tend to be explosive and are difficult to handle [8], hence procedures involving generation of the azides in situ followed by azide alkyne cycloaddition have recently been reported [9][10][11][12][13][14].…”