Porous Metal–Organic Framework Catalyzing the Three-Component Coupling of Sulfonyl Azide, Alkyne, and Amine

Abstract

The robustly porous metal–organic framework MOF–Cu₂I₂(BTTP4) (BTTP4 = benzene-1,3,5-triyl triiso­nicotinate) was shown to work as an efficiently heterogeneous catalyst for the three-component coupling of sulfonyl azides, alkynes, and amines, leading to the formation of <i>N</i>-sulfonyl amidines in good yields. MOF–Cu₂I₂(BTTP4) can be recycled by simple filtration and reused at least four times without any loss in yield. Studies of the ligand effects on the three-component coupling reactions showed that BTTP4 could enhance the rate, as well as the chemoselectivity, when aromatic alkynes were employed. The catalytic process has been thoroughly studied by means of single-crystal and powder X-ray diffraction, gas and solvent adsorption, in situ ¹H NMR and FT-IR spectroscopy, X-ray photoelectron spectra (XPS), and ICP analysis of Cu leaching