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Iron‐Enabled Utilization of Air as the Terminal Oxidant Leading to Aerobic Oxidative Deoximation by Organoselenium Catalysis
Author(s) -
Chen Chao,
Zhang Xu,
Cao Hongen,
Wang Fang,
Yu Lei,
Xu Qing
Publication year - 2019
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.201801163
Subject(s) - chemistry , catalysis , hydrogen peroxide , selenium , pro oxidant , peroxide , oxidative phosphorylation , catalytic cycle , oxygen , x ray photoelectron spectroscopy , reactive oxygen species , photochemistry , organic chemistry , biochemistry , chemical engineering , engineering
In contrast to conventional organoselenium‐catalyzed oxidation reactions that require peroxide oxidants such as hydrogen peroxide, in this work we found that, addition of a low loading of iron (II) could enable the successful utilization of air as the terminal oxidant in organoselenium‐catalyzed oxidative deoximation reaction of ketoximes. This led to a new mild and relatively green aerobic oxidative deoximation method. Control reactions and X‐ray photoelectron spectroscopy (XPS) analysis suggest that iron is crucial in the catalytic cycle, working to prohibit the deactivation of selenium catalyst through an iron‐catalyzed aerobic oxidation of low valent selenium species by air to the active high valent selenium species. Since air can be utilized as the terminal oxidant, this work may contribute to the advance of organoselenium catalysis.