Bioinspired Manganese Complexes and Graphene Oxide Synergistically Catalyzed Asymmetric Epoxidation of Olefins with Aqueous Hydrogen Peroxide. Issue 3 (23rd January 2017)

• Record Type: Journal Article
• Authors: Miao, Chengxia; Yan, Xingbin; Xu, Daqian; Xia, Chungu; Sun, Wei
• Is Part Of: Advanced synthesis & catalysis. Volume 359:Issue 3(2017)
• Page Start: 476
• Page End: 484
• Publication Date: 2017-01-23
• Subjects: aqueous hydrogen peroxide -- asymmetric epoxidation -- bioinspired manganese complexes -- graphene oxide -- synergistically; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600848
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Bioinspired manganese complexes of N4 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 (H2 O2 ) and gives a reasonable rationale for the large consumption of H2 O2 . Also, part of the hydrogen peroxide was used for the oxidation of GO. Abstract :