Copper‐Catalyzed Synthesis of α‐Aryl Ketones by Metal–Organic Framework MOF‐199 as an Efficient Heterogeneous Catalyst

Abstract

A highly crystalline porous copper‐based metal–organic framework MOF‐199 was synthesized from the reaction of 1,3,5‐benzenetricarboxylic acid and copper nitrate trihydrate by a solvothermal method. The MOF‐199 was characterized by several techniques, including X‐ray powder Diffraction (XRD), Scanning Electron Microscopy (SEM), Transmission Electron Microscopy (TEM), Thermogravimetric Analysis (TGA), Fourier Transform‐Infrared (FT‐IR), Atomic Absorption Spectrophotometry (AAS), and nitrogen physisorption measurements. The MOF‐199 proved to be an efficient catalyst for the C‐arylation of aryl iodides with acetylacetone to form α‐aryl ketones as the principal products. The catalyst can be separated from the reaction mixture by simple decantation, and be reused without significant degradation in catalytic activity. No contribution from homogeneous catalysis of active species leaching into the liquid phase was detected, confirming that the MOF‐199 is a truly heterogeneous catalyst.

Direct Oxidative Amidation between N,N‐dimethylanilines and Anhydrides Using Metal‐Organic Framework [Cu2(EDB)2(BPY)] as an Efficient Heterogeneous Catalyst

“…[22,23] Combining some special physical properties of both organic and inorganic porous materials, MOF-based structures exhibit several advantages as compared to conventional materials. [27][28][29] A variety of MOFs have been employed as catalysts or catalyst supports for many organic reactions, ranging from carbon-carbon [30][31][32][33] to carbon-heteroatom forming transformations. [27][28][29] A variety of MOFs have been employed as catalysts or catalyst supports for many organic reactions, ranging from carbon-carbon [30][31][32][33] to carbon-heteroatom forming transformations.…”

New URJC-1 Material with Remarkable Stability and Acid-Base Catalytic Properties

“…The third copper atom is connected to nitrogen N2 atom of a tetrazole ring. The crystal data found for the as-synthesized URJC-1 material are: Mr = 314.25; orthorhombic, Pn21a; a = 8.6577 (6), b = 9.0478(9), c = 14.9973 (11), V = 1174.79 Å 3 ; Z = 4; Dc = 1.77 g/cm 3 . More details of the structural unit of URJC-1 material were included in Figure S1 and Table S1.…”

“…In the last years, copper-based MOF materials with unsaturated metal centers as Lewis acid sites have been studied in several catalytic reactions, like O-arylation of phenols with nitroarenes [11] and Friedel-Crafts acylation [12,13]. Knoevenagel condensation between carbonyl (C=O) and activated methylene groups has also been explored as a feasible catalytic application of MOF materials [14].…”

Highly Efficient and Reusable Microporous Schiff Base Network Polymer as a Heterogeneous Catalyst for CuAAC Click Reaction

“…Heterogeneous catalytic reactions are well established and widespread processes in the field of environment protection overcome the problems associated with the homogeneous counterparts. The use of heterogeneous catalysts in various reactions triggered the exploration of the development of economically and environmentally promising Cu‐based systems since the amount of the leached metal can be significantly reduced . Moreover, these heterogeneous Cu catalysts can offer several advantages, for instance, easy catalyst/product separation, high reusability, and improved stability, as well as high catalytic performance.…”