Copper-complex anchored on SBA-۱۵ for O-Arylation of Phenols via the Ullmann Reaction

Traditionally, copper-catalyzed Ullmann-type conditions have been applied for N- and O-arylation of amines and phenols with haloarenes. Nevertheless, the need for stoichiometric copper compounds, the insolubility of copper (I) salts, and non-reproducible reactions are drawbacks of these protocols. In recent decades, Pd-catalyzed N-arylation of amines and O- arylation of phenols have been developed [۱, ۲]. However, the C-O bond formation via the inexpensive and more practical copper-catalyzed chemistry has been re-noted. The present work describes the synthesis and characterization of a SBA-۱۵-supported Cu(I) catalyst for the C-O bond formation via the Ullmann-type O-arylation reaction between haloarenes and phenols, Scheme ۱.SBA-۱۵ was subsequently treated with (۳-aminopropyl) triethoxysilane, cyanuric chloride, ۲-hydrazinopyridine, and a solution of CuI in acetonitrile to afford SBA- ۱۵@Py-۲-NHNH۲-Cu(I). The supported complex was fully characterized by common methods, e.g. FT-IR, thermogravimetric thermal analysis (TGA), CP MAS ۱۳ CNMR, X-ray photoelectron spectroscopy (XPS), Brunauer–Emmett–Teller (BET), and Energy-dispersive X-ray spectroscopy (EDX). The supported Cu(I) complex was successfully catalyzed the coupling reaction between haloarenes and phenols. The reaction conditions were optimized and diferent derivatives were prepared. The excellent recyclability of the catalyst was shown by small deactivation over seven runs.

کلیدواژه ها:

SBA-۱۵ ، Mesoporous silica ، Supported Cu(I) catalyst ، Ullmann-type reaction