期刊
HELVETICA CHIMICA ACTA
卷 95, 期 10, 页码 1758-1772出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.201200175
关键词
TEMPO-Mediated oxidation; Aerobic oxidation; Oximes; Oxime ethers
资金
- Ministerium fur Innovation, Wissenschaft und Forschung, NRW
TEMPO-Mediated oxidation of hydroxylamines (=hydroxyamines) and alkoxyamines to the corresponding oxime derivatives is reported (TEMPO=2,2,6,6-tetramethylpiperidin-1-yloxy radical; Scheme 2). These environmentally benign oxidations proceed in good to excellent yields (Table 1). For alkoxyamines, oxidation to the corresponding oxime ethers can be performed by using dioxygen as a terminal oxidant in the presence of 510 mol-% of TEMPO or 4-substituted derivatives thereof as a catalyst (Scheme 3 and Table 2). Importantly, benzyl bromides can directly be transformed to oxime ethers via in situ alkoxyamine formation by a nucleophilic substitution followed by TEMPO-mediated oxidation (Scheme 4 and Table 3).
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