I2/Aqueous TBHP-Catalyzed Coupling of Amides with Methylarenes/Aldehydes/Alcohols: Metal-Free Synthesis of Imides

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• 作者：Hariprasad Aruri ; Umed Singh ; Sanjay Kumar ; Manoj Kushwaha ; Ajai Prakash Gupta ; Ram A. Vishwakarma ; Parvinder Pal Singh
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：August 5, 2016
• 年：2016
• 卷：18
• 期：15
• 页码：3638-3641
• 全文大小：372K
• 年卷期：0
• ISSN：1523-7052

文摘

We present a metal-free method for the synthesis of imides by the direct coupling of NH-amides with methylarenes under iodine/aqueous TBHP conditions. The optimized conditions worked very well with benzaldehydes and benzyl alcohol and furnished the corresponding imides in good to excellent yields. A series of control and radical scavenger experiments were also performed, which suggested the involvement of radical pathways. The labeling experiment in the presence of ¹⁸O-labeled H₂O suggested water as a source of oxygen in the imides.