PCy3-assisted Ag(I)-catalyzed click reaction for regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles at room temperature.

Abstract

An approach towards Cu-free click chemistry has been developed in this work. Silver-catalyzed PCy3-ligand-assisted synthesis of 1,4-disubstituted 1,2,3-triazoles at room temperature has been developed. Regioselectivity of the reaction was confirmed from the results of single-crystal X-ray diffraction (SC-XRD) of one of the products. SC-XRD of ex situ-generated Ag-PCy3 complex helped us propose a plausible mechanism for the reaction. This reaction was indicated to exhibit a catalytic activity level similar to that for the in situ-generated complex. The methodology was found to work well with benzyl azides, phenyl azides, terminal alkynes and internal alkynes in aqueous medium. The one-pot three-component reaction leading to 1,2,3-triazole synthesis also proceeded well.