Copper-Catalyzed Reaction of Ketenimine and in Situ Generated Immonium Ion: Access to α,β-Unsaturated Amidines

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• 作者：Bangben Yao ; Chuang Shen ; Zunjun Liang ; Yuhong Zhang
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：February 7, 2014
• 年：2014
• 卷：79
• 期：3
• 页码：936-942
• 全文大小：403K
• ISSN：1520-6904

文摘

A Cu-catalyzed three-component reaction of alkyne, azides (sulfonyl or phosphoryl azides), and N,N-dialkyloxyformamide dialkyl acetal via electrophilic addition of immonium ion to copper ketenimine is reported. This new protocol for the preparation of 伪,尾-unsaturated amidine derivatives appears to offer high yield, mild conditions, and wide substrate scope. The reaction might involve the processes of copper ketenimine intermediate formation, electrophilic addition, and isomerization.