Azido-type-selective triazole formation by iridium-catalyzed cycloaddition with thioalkynes
Kazuya Sugiyama, Yuki Sakata, Takashi Niwa, Suguru Yoshida, Takamitsu Hosoya
Abstract
The iridium-catalyzed azide-thioalkyne cycloaddition was found to proceed much faster with benzyl azide than with phenyl azide. The high azido-type selectivity was also observed in other combinations of azides with different steric environments. This finding enabled the efficient assembly of three azidophilic molecules to triazido platforms by three sequential triazole-forming reactions.
Topics & Concepts
CycloadditionAzideIridiumChemistrySteric effectsTriazoleCatalysisCombinatorial chemistrySelectivityPhotochemistryOrganic chemistryClick Chemistry and ApplicationsChemical Synthesis and AnalysisProtein Degradation and Inhibitors