Macroporous polymer supported azide and nanocopper (I): efficient and reusable reagent and catalyst for multicomponent click synthesis of 1,4-disubstituted-1H-1,2,3-triazoles from benzyl halides

Abstract

Macroporous polymer supported nanoparticles of copper(I) iodide catalyst and macroporous polymer supported azide reagent were used to simplify the synthesis of 1,4-disubstituted-1H-1,2,3-triazoles from various benzyl halides following the green chemistry principles. This new one-pot protocol facilitates the workup of the reaction and provides the products in short times and at high yields. Heterogeneous catalyst and reagent can be reloaded and reused at least for 5 runs without significant decrease in the yields.Electronic supplementary materialThe online version of this article (doi:10.1186/2193-1801-2-64) contains supplementary material, which is available to authorized users.

One-pot multicomponent nitro-Mannich reaction using a heterogeneous catalyst under solvent-free conditions

“…The chelation process takes approximately one day. The nano-sized copper salt so obtained, being immobilised on the terminal nitrogen in the dimethylamino moiety within the ion-exchange polymeric resin, results in an improvement in activity since the surface area for catalytic activity is increased and such chelation also prevents oxidation or disproportionation of the copper (I) ion, which would affect negatively its activity ( Bosica & Gabarretta, 2015 ; Keshavarz et al, 2013 ). Handling of the catalyst is also relatively simple due to the beaded form of the resin and hence, only filtration is required to collect the catalyst after completion of the reaction.…”

Peer Review #2 of "One-pot multicomponent nitro-Mannich reaction using a heterogeneous catalyst under solvent-free conditions (v0.1)"

“…The chelation process Manuscript to be reviewed takes approximately one day. The nano-sized copper salt so obtained, being immobilised on the terminal nitrogen in the dimethylamino moiety within the ion-exchange polymeric resin, results in an improvement in activity since the surface area for catalytic activity is increased and such chelation also prevents oxidation or disproportionation of the copper (I) ion, which would affect negatively its activity [49,54]. Handling of the catalyst is also relatively simple due to the beaded form of the resin and hence, only filtration is required to collect the catalyst after completion of the reaction.…”

Unprecedented one-pot multicomponent synthesis of propargylamines using Amberlyst A-21 supported CuI under solvent-free conditions

“…Nafion NR50, for example has been put forward as a candidate for propargylamine formation, and it was queried whether the SAC-13 form would be viable substitute. 63,64 Given the involvement of alkyne substrates in this reaction, it was postulated that its activity could also be extended to the formation of propargylamines through A 3 -coupling. [60][61][62] It is evident from the outset, however, that the involvement of a copperspecies is quintessential to this reaction proceeding with success.…”

“…63 Immobilisation of the active copper species brought with it numerous benefits (Figure 4). 64 The catalyst itself displayed high stability and could easily be handled in air. This made the catalyst very easy to handle, especially during filtration and recovery steps, and even if some of the catalyst was accidentally dropped onto the bench, recovery was greatly facilitated.…”