Metal-Free Intermolecular Oxidative C鈥揘 Bond Formation via Tandem C鈥揌 and N鈥揌 Bond Functionalization

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• 作者：Abhishek A. Kantak ; Shathaverdhan Potavathri ; Rose A. Barham ; Kaitlyn M. Romano ; Brenton DeBoef
• 刊名：Journal of the American Chemical Society
• 出版年：2011
• 出版时间：December 14, 2011
• 年：2011
• 卷：133
• 期：49
• 页码：19960-19965
• 全文大小：926K
• 年卷期：v.133,no.49(December 14, 2011)
• ISSN：1520-5126

文摘

The development of a novel intermolecular oxidative amination reaction, a synthetic transformation that involves the simultaneous functionalization of both a N鈥揌 and C鈥揌 bond, is described. The process, which is mediated by an I(III) oxidant and contains no metal catalysts, provides a rapid and green method for synthesizing protected anilines from simple arenes and phthalimide. Mechanistic investigations indicate that the reaction proceeds via nucleophilic attack of the phthalimide on an aromatic radical cation, as opposed to the electrophilic aromatic amination that has been reported for other I(III) amination reactions. The application of this new reaction to the synthesis of a variety of substituted aniline derivatives is demonstrated.