Synthesis and properties study of novel ferrocenyl isoxazole derivatives

Abstract

A synthetic procedure based on the 1,3-dipolar cycloaddition reactions of nitrile oxides and ethynylferrocene derived from ferrocene has been developed to synthesize new ferrocenyl-isoxazole derivatives. The stable solids were thoroughly characterized by 1 H NMR, FT-IR, and mass spectroscopy. The structure of (η 5 -C 5 H 5 ) Fe (η 5 -C 5 H 4 ) C 3 HNOC 6 H 4 CH 3 was determined by singlecrystal X-ray diffraction. The electrochemical behaviors of the synthesized ferrocenyl-isoxazole derivatives were also studied.

Novel isoxazoline ligand with ferrocene backbone: preparation and application in Heck reaction with water as solvent

“…In our method, the reactions of disubstituted alkenes with aryl iodides proceeded smoothly to produce the desired trisubstituted alkenes with satisfactory yield at a slightly higher temperature (entries 20–24). Compared to the ferrocenylisoxazole ligand reported by our group previously, 7c the newly developed catalytic system offers a much milder approach, with a broader substrate scope, giving coupling compounds with higher yields under much lower catalyst loading.…”

“…Novel isoxazoline ligands with a ferrocene backbone were synthesized following a method reported by our group previously, and the procedure for 1,3‐bis‐(5‐ferrocenylisoxazoline‐3‐yl)benzene 4 is shown in Scheme as representative’. Its structure was unambiguously confirmed by X‐ray diffraction analysis, which was in accordance with NMR, IR and mass spectra.…”

“…Prompted by the potential performance of isoxazol(in)e ligand and the unique character of ferrocenyl substituent in the catalytic cycle, our group have initiated a program dealing with ferrocenylisoxazole derivatives since 2006, and have reported the synthesis of a series of ferrocenyl‐substituted isoxazole compounds. Further explorations have demonstrated their satisfactory performance as ligands in palladium‐catalyzed C−C bond formation reactions under phosphine‐free conditions . As part of our ongoing quest to find new ferrocene ligands, we herein wish to report the synthesis of ferrocenylisoxazoline ligands and further explored their catalytic utility in palladium‐catalyzed Heck reactions.…”

A Modified Glassy Carbon Electrode for Hydrogen Peroxide Sensing

“…Therefore, the substituted group on the ferrocene would affect the redox of ferrocene derivatives. 25 …”

Phosphoramides bearing isoxazole derivative: spectroscopic and structural characterization, study of hydrogen-bonding interactions and two lanthanide complexes (LnIII= Ce and Eu)

“…Furthermore, the isoxazole heterocycles have been considered as notable synthetic tools in organic synthesis, since the weak nitrogen-oxygen bond is easily cleavable under certain experimental conditions (Pinho e Melo, 2005;Shang et al, 2006). Hence, the chemistry of isoxazoles and the preparation of new compounds of this family is of scientific interest.…”