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Bioinspired Manganese Complexes and Graphene Oxide Synergistically Catalyzed Asymmetric Epoxidation of Olefins with Aqueous Hydrogen Peroxide
Author(s) -
Miao Chengxia,
Yan Xingbin,
Xu Daqian,
Xia Chungu,
Sun Wei
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600848
Subject(s) - chemistry , hydrogen peroxide , catalysis , acetic acid , enantioselective synthesis , oxide , chalcone , x ray photoelectron spectroscopy , manganese , aqueous solution , graphene , medicinal chemistry , organic chemistry , nanotechnology , materials science , physics , nuclear magnetic resonance
Bioinspired manganese complexes of N 4 ligands and graphene oxide (GO) synergistically catalyze the highly enantioselective epoxidation of olefins (up to 99% ee ), which is a rare example with GO as a co‐catalyst in asymmetric catalysis. GO as a new and key additive not only successfully functions in catalytic amounts, but also has a positive effect for improving the enantioselectivity of the asymmetric epoxidation compared with the traditional stoichiometric organic carboxylic acid method [e.g., chalcone, 95% ee (3.5 mg GO) vs . 84% ee (5 equiv., 75 mg acetic acid), ethyl cinnamate, 84% ee (3.5 mg GO) vs . 19% ee (5 equiv., 75 mg acetic acid)]. The X‐ray photoelectron spectroscopy (XPS) spectra of GO before and after the reaction indicate that the intensities of C–O become stronger after the reaction, which may have a certain relationship with hydrogen peroxide (H 2 O 2 ) and gives a reasonable rationale for the large consumption of H 2 O 2 . Also, part of the hydrogen peroxide was used for the oxidation of GO.