Abstract
In this report, novel glycosylpyridyl-triazole@nickel nanoparticles (GPT-Ni) were successfully prepared via click chemistry and were fully characterized by various spectroscopy measurements. The as-prepared catalysts could be used as a recyclable catalyst for the catalytic acylation of amines by employing N,N-dimethylacetamide (DMA), N,N-dimethylpropionamide (DMP), and N,N-dimethylformamide (DMF) as acylation reagents in water, providing the corresponding amides in good yields. The practicability of this methodology is highlighted by the good recyclability of the catalyst. A unique mechanism was proposed for the catalytic process.
Highlights
Amides are essential components in the fine chemical industry because they are frequently encountered backbones in agricultural chemicals, pharmaceuticals, and natural products [1,2,3].Traditionally, the construction of amides mainly focus on the acylation of amines by employing acyl chloride, carboxylic acid, and anhydride, as well as ester [4,5,6]
We reported an efficient method for the synthesis of glycosylpyridyl-triazole@nickel nano catalysts (GPT-Ni) which were fully characterized by high resolution mass spectrum (HRMS), X-ray diffraction (XRD), infrared spectroscopy (IR), thermogravimetric analysis (TG), and transmission electron microscopy (TEM)
When the reaction of NiCl2 (1.0 equiv.) and glycosyl pyridyl-triazole (1.2 equiv.) was set up, a glycosylpyridyl-triazole@nickel nanoparticles (GPT-Ni) formulated as dimer was obtained as the sole product, which was characterized by HRMS and IR [34]
Summary
Amides are essential components in the fine chemical industry because they are frequently encountered backbones in agricultural chemicals, pharmaceuticals, and natural products [1,2,3]. Great interest has been devoted to the development of novel catalytic approaches that would allow the highly selective and environmentally friendly preparation of amides [8,9,10,11,12]. Following the great progress in cross-coupling reactions using precious metal catalysts, novel methods that utilize cheap and widely abundant metals has become an important research area [13,14,15,16]. There is tremendous potential for the development of efficient approaches using non-precious metals and great demand for improving reaction scope, decreasing catalyst loading and improving catalyst stability. Our group has prepared a highly active and recoverable heterogeneously sugar-based palladium catalysts which have been used for solvent-free Mizoroki-Heck reactions [34] and aqueous phase Suzuki-Miyaura couplings (Scheme 1a) [35]. Mizoroki-Heck reactions and GPT-Pd catalyzed Suzuki-Miyaura couplings; (b) GPT-Ni catalyzed acylation of amines
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