A tris(benzyltriazolemethyl)amine-based cage as a CuAAC ligand tolerant to exogeneous bulky nucleophiles

Abstract

The archetypal tris(benzyltriazolemethyl)amine (TBTA) ligand was equipped with a bowl-shaped cap in the cage Hm-TBTA. Hm-TBTA accelerates CuAAC reactions without suffering from product inhibition. Furthermore, this shielded ligand efficiently protects the copper center from deactivation by the Cu^I–chelator glutathione, opening the way to novel approaches for efficient CuAAC reactions in complex media.