Ultrasound Assisted High-Throughput Synthesis of 1,2,3-Triazoles Libraries: A New Strategy for "Click" Copper-Catalyzed Azide-Alkyne Cycloaddition Using Copper(I/II) as a Catalyst

A series of 1,4-disubstituted 1,2,3-triazoles were prepared by a parallel synthesis protocol utilizing the 3D-supramolecular coordination polymer (SCP) {[Cu-I(CN)(phen)(2)Cu-II(CN)(2)(phen)]5H(2)O}, 1 as a catalyst under ultrasonic irradiations. This work establishes the synergistic action between the mixed valance copper catalyst SCP 1 and ultrasonic irradiation to yield a high-throughput synthesis of 1,4-disubstituted 1,2,3-triazoles libraries. This mixed valance copper(I/II) supramolecular coordination polymer catalyzed azide alkyne cycloaddition reaction protocol allowed a rapid synthesis of the target compounds (10min) in a parallel fashion with good to excellent yields. Twelve reactions were performed in a single deep well microtiter plate, employing three alkynes and four different azide reagents. From this effort, a total of twelve 1,2,3-triazole were obtained in useful isolated yields. Moreover, unambiguous structural assignment of the obtained regioisomers was determined utilizing Heteronuclear Multiple Bond Correlation (HMBC) 2D NMR techniques as a valuable.Graphical AbstractA series of 1,4-disubstituted 1,2,3-triazoles were prepared by a parallel synthesis protocol utilizing the 3D-supramolecular coordination polymer (SCP) {[Cu-I(CN)(phen)(2)Cu-II(CN)(2)(phen)]5H(2)O}, 1 as a catalyst under ultrasonic irradiations. [GRAPHICS] .