Metal–Organic Framework MIL-101-NH₂-Supported Acetate-Based Butylimidazolium Ionic Liquid as a Highly Efficient Heterogeneous Catalyst for the Synthesis of 3-Aryl-2-oxazolidinones

Abstract

A novel heterogeneous catalyst, the ionic liquid (IL) of 1-butyl-3-methylimidazolium acetate (BmimOAc) immobilized on MIL-101-NH2, denoted as IL­(OAc–)-MIL-101-NH2, was prepared by the “ship-in-a-bottle” strategy. The IL of BmimOAc was prepared in the MIL-101-NH2 nanocages primordially, in which the condensation product of MIL-101-NH2’s amine group with 1,1′-carbonyldiimidazole (CDI) reacted with 1-bromo butane, and then the intermediate exchanged with potassium acetate. The structure and physicochemical properties of IL­(OAc–)-MIL-101-NH2 were characterized by powder X-ray diffraction, scanning electron microscopy, Fourier transform infrared spectroscopy, DRS UV–vis, nitrogen adsorption–desorption, and elemental analysis. The results indicated that BmimOAc was anchored in the MIL-101-NH2 skeleton via the acylamino group and confined in the nanocages in the form of a single molecule. The composite material of IL­(OAc–)-MIL-101-NH2 exhibited excellent catalytic activity and catalytically synthesized 3-aryl-2-oxazolone in an excellent yield of 92%. It can be reused up to six times without noteworthy loss of its activity and demonstrated distinct size-selective property for substrates. It was conjectured that the diffusion kinetics of reactants could be controlled by the aperture size of the metal–organic framework support.

Recent Advances in the Synthesis and Ring‐Opening Transformations of 2‐Oxazolidinones

“…In 2019, Ji and co‐workers utilized the metal‐organic framework MIL‐101‐NH 2 ‐supported BmimOAc heterogeneous catalyst, for the effective synthesis of bioactive 3‐aryl‐2‐oxazolidinones (Scheme 35). [58] This excellent composite catalyst system significantly exhibited superior catalytic activity and wide substrate scope for the preparation of a wide range of N ‐aryl‐2‐oxazolidinones 122 with good to excellent yields. Importantly, it can be recycled up to six times without obvious loss of its activity.…”

The production of clean diesel fuel by facile sun light photocatalytic desulfurization process using Cd-based diacetate as a novel liquid photocatalyst

“…The catalytic activity is not only due to the metal but also its chemical state: acetate groups change the DRS properties and photocatalytic efficiency. Chong et al reported the contribution of acetate groups for reducing the band-gap and then on the shift of the wavelength toward higher values (visible regions) (Chong et al, 2019). Moreover, the dispersion of the Cd complex in the diesel phase under agitation may allow a better availability of catalytic sites.…”

Copper and nickel immobilized on cytosine@MCM‐41: as highly efficient, reusable and organic–inorganic hybrid nanocatalysts for the homoselective synthesis of tetrazoles and pyranopyrazoles

“…[1][2][3][4][5][6][7] Therefore, nanoparticles have been widely used as solid supports for the immobilization of homogeneous catalysts. [8][9][10] For example, silica materials, [11] polymers, [12] graphene oxide, [13][14][15][16] carbon nanotubes, [17] iron oxide, [18] ionic liquids, [19,20] boehmite nanoparticles, [21,22] biochar, [23] magnetic nanoparticles, [24][25][26] etc. were employed as support for the stabilization of homogeneous catalysts.…”