DABCO-Based Ionic Liquids: Recyclable Catalysts for Aza-Michael Addition of 伪,尾-Unsaturated Amides under Solvent-Free Conditions

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• 作者：Anguo Ying ; Zhifeng Li ; Jianguo Yang ; Shuo Liu ; Songlin Xu ; Hua Yan ; Chenglin Wu
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：July 18, 2014
• 年：2014
• 卷：79
• 期：14
• 页码：6510-6516
• 全文大小：392K
• ISSN：1520-6904

文摘

An array of novel 1,4-diazobicyclo[2.2.2]octane (DABCO) based ionic liquids were developed and used as recyclable catalysts for the aza-Michael addition at room temperature without any organic solvent. [DABCO鈥揚DO][OAc] was found to be the most efficient catalyst, and the amount of catalyst was only 10 mol %. Various amines reacted with a wide range of 伪,尾-unsaturated amides, smoothly affording target products in good to excellent yields within hours. Moreover, the catalyst could be reused up to eight times, still maintaining a high catalytic activity. Finally, a plausible mechanism was proposed. FTIR and computational chemistry were used to verify the catalytic mechanism.