A click-based modular approach to introduction of peroxides onto molecules and nanostructures

Alissa Horn, Patrick H. Dussault

Research output: Contribution to journalArticlepeer-review

Abstract

Copper-promoted azide/alkyne cycloadditions (CuAAC) are explored as a tool for modular introduction of peroxides onto molecules and nanomaterials. Dialkyl peroxide-substituted alkynes undergo Cu(i)-promoted reaction with azides in either organic or biphasic media to furnish peroxide-substituted 1,2,3-triazoles. Heterolytic fragmentation of the peroxide to an aldehyde, a side reaction that appears to be related to the formation of the triazole, can be suppressed by use of excess alkyne, the presence of triethylsilane, or by use of iodoalkyne substrates. Complementary reactions of simple alkynes with azido-substituted peroxides are much less efficient. Click reactions of alkynyl peroxyacetals are also reported; reductive fragmentation can be minimized by increasing the distance between the peroxyacetal and the alkyne. The strategy enables modular introduction of dialkyl peroxides and peroxyacetals onto gold nanoparticles, the first such process to be reported.

Original languageEnglish (US)
Pages (from-to)44408-44429
Number of pages22
JournalRSC Advances
Volume10
Issue number72
DOIs
StatePublished - Nov 20 2020

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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