DABCO-Based Ionic Liquids: Recyclable Catalysts for Aza-Michael Addition of α,β-Unsaturated Amides under Solvent-Free Conditions
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–PDO][OAc] was found to be the most efficient catalyst, and the amount of catalyst was only...
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| Veröffentlicht in: | Journal of organic chemistry 2014-07, Vol.79 (14), p.6510-6516 |
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| container_issue | 14 |
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| container_title | Journal of organic chemistry |
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| creator | Ying, Anguo Li, Zhifeng Yang, Jianguo Liu, Shuo Xu, Songlin Yan, Hua Wu, Chenglin |
| description | 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–PDO][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 α,β-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. |
| doi_str_mv | 10.1021/jo500937a |
| format | Article |
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Org. Chem</addtitle><date>2014-07-18</date><risdate>2014</risdate><volume>79</volume><issue>14</issue><spage>6510</spage><epage>6516</epage><pages>6510-6516</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>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–PDO][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 α,β-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. 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| title | DABCO-Based Ionic Liquids: Recyclable Catalysts for Aza-Michael Addition of α,β-Unsaturated Amides under Solvent-Free Conditions |
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