Tripodal Amine Ligands for Accelerating Cu-Catalyzed Azide-Alkyne Cycloaddition: Efficiency and Stability against Oxidation and Dissociation.

ABSTRACT: Ancillary ligands, especially the tripodal ligands such as tris(triazolylmethyl)amines, have been widely used to accelerate the Cu-catalyzed azide-alkyne cycloaddition (CuAAC, a "click" reaction). However, the relationship between the activity of these Cu(I) complexes and their stability against air oxidation and ligand dissociation/exchange was seldom studied, which is critical for the applications of CuAAC in many biological systems. In this work, we synthesized twenty-one Cu(I) tripodal ligands varying in chelate arm length (five to seven atoms), donor groups (triazolyl, pyridyl and phenyl), and steric hindrance. The effects of these variables on the CuAAC reaction, air oxidation, and ligand dissociation were evaluated. Reducing the chelate arm length to five atoms, decreasing steric hi

SUBMITTER: Zhu Z 

PROVIDER: S-EPMC5679428 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature