2024 : 12 : 23
Mehdi Irani

Mehdi Irani

Academic rank: Associate Professor
ORCID:
Education: PhD.
ScopusId: 25630519900
HIndex:
Faculty: Faculty of Science
Address: University Of Kurdistan, Sanandaj, P. O. Box: 416, Iran
Phone: +989128018046

Research

Title
Copper-catalyzed simultaneous dehydrogenation and enantioselective allylic oxidation of alkanes using chiral heterogeneous ligands to produce allylic esters and theoretical investigation of the mechanism
Type
JournalPaper
Keywords
Chiral heterogeneous oxazoline-based ligands, Simultaneous dehydrogenation and enantioselective allylic oxidation, Allylic ester, Computational study, Density functional theory.
Year
2024
Journal Apllied Organometalic Chemsitry
DOI
Researchers Shiva Majidian ، Hersh Ibrahim Rashid ، Yunes Naghdi ، Mehdi Irani ، Saadi Samadi

Abstract

A new asymmetric method for preparing chiral allylic esters from various unactivated alkanes through simultaneous dehydrogenation and enantioselective allylic oxidation in the presence of chiral heterogeneous oxazoline-based ligands is reported for the first time. For this purpose, chiral amino oxazoline ligands, synthesized from chiral amino alcohols and cyanogen bromide, were immobilized on modified MCM-41 mesoporous silica. These chiral heterogeneous ligands were then characterized using Fourier-transform infrared spectroscopy, thermogravimetric analysis, X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy, and Brunauer-Emmett-Teller and Barrett-Joyner-Halenda techniques. Finally, copper-complexes of these ligands were employed in the synthesis of chiral allylic esters, achieving the best result with a %90 yield and %77 enantiomeric excess. Evaluation of the recyclability of the chiral heterogeneous catalysts revealed that they can be reused three times without a noticeable reduction in the results. In addition, the mechanism of formation of the chiral allylic esters was investigated using a density functional theory method.