An Efficient Supported Cu(I) Catalyst for the Amination of Aryl Halides With Sodium Azide

Abstract

We present the synthesis and characterization of a new Cu(I) complex supported on SBA-15 as a catalyst for preparing anilines from the reaction of aryl halides with sodium azide. The SBA-15 support was modified by treating it sequentially with (3-aminopropyl) triethoxysilane (APTES), cyanuric chloride, and 2-aminothiazole (AT). The modified mesoporous silica, SBA-15@BAT, was then treated with a CuI solution in acetonitrile to give SBA-15@BAT-Cu(I). The catalyst underwent thorough characterization using conventional methods. X-Ray photoelectron spectroscopy (XPS) analysis corroborated the presence of copper in the +1 oxidation state in the catalyst. The supported Cu(I) complex sufficiently catalyzed the amination reaction of iodo-, bromo-, and chloroarenes with NaN3. The catalyst was centrifuged, washed, and applied in the subsequent run. We investigated the effects of various reaction components and parameters to determine the optimal conditions for the reaction. The heterogeneous catalyst exhibited noticeable stability and was reused over seven runs with slight deactivation. Supporting and characterization of a new Cu(I) catalyst catalyst based on 2-aminothiazole-Cu(I) on SBA-15. Optimization of the reaction conditions for the supported catalyst in the amination of haloarens with sodium azide. Preparation of a wide range of anilines from chloro-, bromo-, and iodoarens. image