Remote C(sp3)–H Oxygenation of Protonated Aliphatic Amines with Potassium Persulfate

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• 作者：Melissa Lee ; Melanie S. Sanford
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：February 3, 2017
• 年：2017
• 卷：19
• 期：3
• 页码：572-575
• 全文大小：332K
• ISSN：1523-7052

文摘

This letter describes the development of a method for selective remote C(sp³)–H oxygenation of protonated aliphatic amines using aqueous potassium persulfate. Protonation serves to deactivate the proximal C(sp³)–H bonds of the amine substrates and also renders the amines soluble in the aqueous medium. These reactions proceed under relatively mild conditions (within 2 h at 80 °C with amine as limiting reagent) and do not require a transition metal catalyst. This method is applicable to a variety of types of C(sp³)–H bonds, including 3°, 2°, and benzylic C–H sites in primary, secondary, and tertiary amine substrates.