Facile azide formation via diazotransfer reaction in a copper tube flow reactor

A Practical Guide on the Synthesis of Metal Chelates for Molecular Imaging and Therapy by Means of Click Chemistry

“…[10] Overall, it might have been more than just am arginal impetus for the remarkable dissemination and success of click chemistry that ah uge varietyo fa lkyne-or azide-functionalized molecules for CuAAC as well as SPAAC, such as functional peptides, saccharides, dyes, fluorophors,l inkers, chelators, PEGylation agents, etc.,h ave meanwhile been made commercially availableb ys pecialized suppliers. [12] Of course, this progress did not go unnoticed by radiopharmacists,a nd click chemistry was quickly adapted for introduction of radionuclides into pharmaceutically active molecules in order to obtain radiotracers for nuclear imaging. In addition, novel practical methods for synthesis of azide-o ra lkyne-decorated functional molecules are continuously being developed, [6] for example, the direct conversion of the N-terminus of ar esin-bound peptidei nto an azide, which provides facile access to clickablep eptides withoutt he necessity of coupling extra buildingb locks, [11] or the continuous synthesis of azides from primary amines by diazo transfer in ac opper-tubeflow reactor.…”

“…Researchers nowadays have immediate access to an immensely large toolbox of clickable building blocks, greatly facilitating the rapid assembly of multifunctional constructs for biomedical applications or materials science. In addition, novel practical methods for synthesis of azide‐ or alkyne‐decorated functional molecules are continuously being developed, for example, the direct conversion of the N ‐terminus of a resin‐bound peptide into an azide, which provides facile access to clickable peptides without the necessity of coupling extra building blocks, or the continuous synthesis of azides from primary amines by diazo transfer in a copper‐tube flow reactor …”

Gadolinium(III)-DOTA Complex Functionalized with BODIPY as a Potential Bimodal Contrast Agent for MRI and Optical Imaging

“…We have recently shown that BODIPY dyes can be functionalized in a copper tube flow reactor via chemistry that converts primary amines into azides using the catalyst generated in situ from the metallic copper [55]. In this paper we further expand this strategy for performing azide-alkyne cycloaddition in order to create a Gd-DOTA-BODIPY derivative.…”

Discovery of bioactive molecules from CuAAC click-chemistry-based combinatorial libraries

“…Alternatively, diverse azides or alkyne building blocks with various linker lengths, degree of steric hindrance and polarity values can easily be accessed in a parallel manner from common precursors using standard literature procedures [65]. If necessary, the synthetic method should be optimized to avoid the use of protecting groups.…”