• 文献标题:   Chirally modified cobalt-vanadate grafted on battery waste derived layered reduced graphene oxide for enantioselective photooxidation of 2-naphthol: Asymmetric induction through non-covalent interaction
  • 文献类型:   Article
  • 作  者:   BARUAH MJ, BORA TJ, GOGOI G, HOQUE N, GOUR NK, BHARGAVA SK, GUHA AK, NATH JK, DAS B, BANIA KK
  • 作者关键词:   cobaltvanadium oxide, cinchonidine, chiral schiff base, asymmetric synthesi, binol
  • 出版物名称:   JOURNAL OF COLLOID INTERFACE SCIENCE
  • ISSN:   0021-9797 EI 1095-7103
  • 通讯作者地址:  
  • 被引频次:   2
  • DOI:   10.1016/j.jcis.2021.10.091 EA NOV 2021
  • 出版年:   2022

▎ 摘  要

The cobalt oxide-vanadium oxide (Co3O4-V2O5) combined with reduced graphene oxide (rGO) having band gap of ti 3.3 eV appeared as a suitable photocatalyst for selective oxidation of 2-naphthol to BINOL. C2-symmetric BINOL was achieved with good yield using hydrogen peroxide as the oxidant under UV-light irradiation. The same catalyst was chirally modified with cinchonidine and a newly synthesized chiral Schiff base ligand having a sigma-hole center. The strong interaction of the chiral modifiers with the cobalt-vanadium oxide was truly evident from various spectroscopic studies and DFT calculations. The chirally modified mixed metal oxide transformed the oxidative CAC coupling reaction with high enantioselectivity. High enantiomeric excess upto 92 % of R-BINOL was obtained in acetonitrile solvent and hydrogen peroxide as the oxidant. A significant achievement was the formation of S-BINOL in the case of the cinchonidine modified catalyst and R-BINOL with the Schiff base ligand anchored chiral catalyst. The UV-light induced catalytic reaction was found to involve hydroxyl radical as the active reactive species. The spin trapping ESR and fluorescence experiment provided relevant evidence for the formation of such species through photodecomposition of hydrogen peroxide on the catalyst surface. The chiral induction to the resultant product was found to induce through supramolecular interaction like O-H...1C, H...Br interaction. The presence of sigma hole center was believed to play significant role in naphtholate ion recognition during the catalytic cycle. (c) 2021 Elsevier Inc. All rights reserved.