Nickel containing ionic liquid based ordered nanoporous organosilica: a powerful and recoverable catalyst for synthesis of polyhydroquinolines

Abstract

The synthesis, characterization and catalytic application of a novel nickel containing ionic liquid based ordered mesoporous organosilica are demonstrated.

Recent advanced development of metal-loaded mesoporous organosilicas as catalytic nanoreactors

“…For the preparation of metal complex-bearing PMO heterogeneous catalysts, metal loading mainly relies on the number of functional groups on PMO. 146,175,192,253 The distribution of metal species on the PMO is governed by the distribution of functional groups on PMO. Only functional groups uniformly distributed over the mesopore surface or the external surface are available to coordinate with metal complexes and to form active metal sites for catalysis.…”

“…29 ). 175 A Ni@IL-PMO-catalyzed four-component Hantzsch reaction of ethyl/methylacetoacetate, dimedone, aldehyde and ammonium acetate was performed at 70 °C for the desired time under solvent-free conditions. Under the optimized reaction conditions, polyhydroquinolines were obtained in high to excellent yields and selectivities in the presence of a low loading of Ni@IL-OMO with short reaction times, while Ni@IL-PMO still retained efficient catalytic activity after the 9th run.…”

“…227 Copper acetate was linked to imidazolium ionic liquid-modified phenylene-bridged PMO to form copper-loaded bifunctional PMO (Cu@BPMO-Ph-IL). As Ni@IL-PMO, 175 catalyst Cu@BPMO-Ph-IL promoted the four-component Hantzsch reaction of ethyl/methylacetoacetate, dimedone, aldehyde and ammonium acetate to polyhydroquinolines denoted as Ni@IL-PMO, 175 and gave a good catalytic activity, easy separation and reusability, due to the high stability of the mesoporous structure. 228 Furthermore, copper nitrate was anchored to alkyl imidazolium-bridged PMO (PMO-IL) to afford a copper-bonded PMO-IL nanocatalyst (Cu@PMO-IL).…”

The Recent Progress on Supported and Recyclable Nickel Catalysts towards Organic Transformations: A Review

“…Recently, Elhamifar et al. reported another convenient solvent‐free method for the synthesis of polyhydroquinolines by using organosilica‐ supported nickel catalyst [63] . The nanocatalyst demonstrated excellent performances towards recyclability, easy work‐up, operation simplicity and most importantly absence of unwanted products.…”

Application of [Fe3O4@SiO2@(CH2)3Py]HSO4− as heterogeneous and recyclable nanocatalyst for synthesis of polyhydroquinoline derivatives

“…[3][4][5][6][7][8] Despite of a variety of applications for polyhydroquinoline derivatives, very few approaches have been established for the synthesis of these compounds. In recent years, more efficient catalysts have been reported for the synthesis of polyhydroquinolines, such as baker's yeast, [10] Ce(NH 4 ) 2 (NO 3 ) 6 , [11] glycine, [12] grinding, [13] hafnium (IV) bis(perfluorooctanesulfonyl)imide complex in fluorous media, [14] Ni 0.35 Cu 0.25 Zn 0.4 Fe 2 O 4 magnetic nanoparticles (MNPs), [15] Hy-Zeolite, [16] Cu-S-(propyl)-2aminobenzothioate, [17] L-proline and derivatives, [10] metal triflates, [18] molecular iodine, [19] Fe 3 O 4 -adenine-Ni, [20] 4,4′-(butane-1,4-diyl)bis(1-sulfo-1,4-diazabicyclo [2.2.2] octane-1,4-diium)tetrachloride, [21] PTSA, [22] solar thermal energy, [23] MCM-41@Serine@Cu(II), [24] MNPs/DETA-SA, [25] Ni-Cu-Mg Fe 3 O 4 MNPs, [26] ILOS@Fe/TSPP, [27] alginic acid, [28] Ni@IL-OMO, [29] V-TiO 3 [30] and melamine trisulfonic acid. [9] However, this method has some disadvantages like the harsh conditions of the reaction, tedious workup procedure, low yields, use of large quantities of volatile organic solvent and long eaction times.…”