Synthesis of new TCH/Ni‐based nanocomposite supported on SBA‐15 and its catalytic application for preparation of benzimidazole and perimidine derivatives

Abstract

A stable nickel‐decorated SBA‐15 nanocomposite (Ni/TCH@SBA‐15) was synthesized through surface modification of silica nanoparticles with 3‐chloropropyltriethoxysilane (CPTES) and thiocarbohydrazide (TCH) followed by metal–ligand coordination with Ni (II). The structure of this organometallic nanocomposite was characterized by Fourier transform‐infrared, field emission‐scanning electron microscopy, EDAX, transmission electron microscopy, atomic absorption spectroscopy and N2 adsorption–desorption (Brunauer–Emmett–Teller) techniques. The catalytic performance of Ni/TCH@SBA‐15 (NNTS‐15) was determined for the synthesis of 2‐aryl‐substituted benzimidazoles and 2,3‐dihydroperimidines. The excellent yields within shorter reaction times, simplicity of catalytic methods, non‐toxicity and clean reactions, mild reaction conditions and easy work‐up procedure are the important merits of these synthetic protocols. Moreover, the Ni (II) bonded to the SBA‐15 surface was stable under the catalytic reaction conditions resulting in its efficient recycling and reuse.

Pd Doped on TCH@SBA-15 Nanocomposites: Fabrication and Application as a New Organometallic Catalyst in the Three-Component Synthesis of N-Benzo-imidazo- or -thiazole-1,3-thiazolidinones

“…The organometallic nanohybrid composite Pd/TCH-pr@SBA-15 was designed and fabricated according to Scheme 2. SBA-15 was functionalized with the organosilane precursor 3chloropropyltriethoxysilane according to the reported method by Kalhor et al (2019). Then, this chloropropyl-grafted SBA-15 was refluxed with a TCH ligand followed by complexation with Pd(OAc) 2 to afford the supported Pd catalyst on the SBA-15 nanoparticles.…”

“…The Typical Procedure for the Synthesis of Pd/TCH-pr@SBA-15 Nanocatalysts Chloropropyl-functionalized SBA (Pr-Cl@SBA-15) was prepared according to the literature by Kalhor et al (2019). Then, for the synthesis of TCH/Pr-Cl@SBA-15 nanohybrids, in a 100 ml round-bottom flask, 1.2 g (11.3 mmol) of TCH was dissolved in 18 ml of acetonitrile and stirred for 1 h. Next, 1.17 g (6.67 mmol) of KI and 1.2 g of SBA-15-Cl were added to the reaction mixture and refluxed for 15 h. The solvent was removed, and the mixture was collected using a centrifuge.…”

“…Considering the above points in our ongoing research on the synthesis of organometallic nanocatalysts (Kalhor et al, 2019;, we report herein a simple method for the preparation of stable and active Pd supported on TCH@SBA-15 mesoporous composites as a nanocatalyst for the threecomponent synthesis of 2-aryl-N-benzo-imidazo-or -thiazole-1,3-thiazolidinones via condensation of the aldehyde derivatives 2-aminobenzimidazole or benzothiazole and thioglycolic acid under green conditions (Scheme 1).…”

Copper(II) Oxide Nanoparticles Impregnated on Melamine‐Modified UiO‐66‐NH2 Metal–Organic Framework for C–N Cross‐Coupling Reaction and Synthesis of 2‐Substituted Benzimidazoles

“…Although these inorganic porous materials (e.g. SBA‐15 , MCM‐41 , zeolite , and alumina ) possess high thermal and mechanical stabilities, their preparations require soft or hard templates as structural‐directing agents to ensure the pore formation. Moreover, they are prepared via a multistep energy‐consuming process: solvothermal reaction (e.g.…”

Recent Advances in the Synthesis of Perimidines and their Applications

“…This method included some interesting features like eco-friendliness, simple procedure, high yields with purity, atom economy, and recyclable catalyst (Scheme 9, Method 6). Kalhor et al [101] investigated a green nano-catalyzed synthesis of 2,3-dihydroperimidines in excellent yields from NDA and various aldehydes in EtOH with stirring at room temperature using nickel-decorated SBA-15 nanocomposite (Ni/TCH@ SBA-15). This methodology is highly convenient due to several advantages like clean reaction process, mild conditions, simple work-up, no need of further purification, high yield and purity in minutes, easy recoverability, and a reusable heterogeneous catalyst (Scheme 9, Method 7).…”