期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 77, 期 16, 页码 7005-7022出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo3012336
关键词
-
资金
- National Institutes of General Medical Sciences [GM-49093]
The highly regio- and chemoselective oxidation of activated C-H bonds has been observed via copper-catalyzed reactions of oxaziridines. The oxidation proceeded with a variety of substrates, primarily comprising allylic and benzylic examples, as well as one example of an otherwise unactivated tertiary C-H bond. The mechanism of the reaction is proposed to involve single-electron transfer to the oxaziridines to generate a copper-bound radical anion, followed by hydrogen atom abstraction and collapse to products, with regeneration of the catalyst by a final single-electron transfer event. The involvement of allylic radical intermediates was supported by a radical-trapping experiment with TEMPO.
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