{"title":"硝酸钇促进胺的选择性氰乙化","authors":"Arunava Misra, SK Rajibul Haque, Mohabul A Mondal","doi":"10.1007/s12039-023-02173-2","DOIUrl":null,"url":null,"abstract":"<div><p>The catalyst Y(NO<sub>3</sub>)<sub>3</sub>, 6H<sub>2</sub>O exhibited remarkable activity in the aza-Michael addition of various aromatic and aliphatic amines with acrylonitrile at ambient temperature in a protic solvent. The method is selective for the monocyanoethylation of primary aromatic amines, aliphatic secondary amines, and sterically hindered aliphatic amines. Phenols and active methylene compounds do not undergo cyanoethylation. Thiophenol, in the presence of yttrium nitrate, promotes the polymerization of acrylonitrile. The water solubility and high catalyst stability make the process of removing the catalyst from the product easy. Direct aqueous workup of the reaction mixture could lead to the isolation of cyanoethylation products up to 99.9% purity.</p><h3>Graphical Abstract</h3>\n <ul>\n <li>\n <p>Selective <i>mono-</i>cyanoethylation at the primary aromatic amine, especially electron-rich aromatic amines</p>\n </li>\n <li>\n <p>Excellent regio-selectivity in the presence of Carbon and Oxygen nucleophiles</p>\n </li>\n <li>\n <p>The reported condition could be used to polymerize acrylonitrile in the presence of thiophenol.</p>\n </li>\n <li>\n <p>Reaction is facile for electron-rich aromatic amine.</p>\n </li>\n <li>\n <p>Highly sensitive to the steric effect at the nitrogen center</p>\n </li>\n </ul>\n <figure><div><div><div><picture><img></picture></div></div></div></figure>\n </div>","PeriodicalId":50242,"journal":{"name":"Journal of Chemical Sciences","volume":"135 3","pages":""},"PeriodicalIF":1.7000,"publicationDate":"2023-06-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Yttrium nitrate promoted selective cyanoethylation of amines\",\"authors\":\"Arunava Misra, SK Rajibul Haque, Mohabul A Mondal\",\"doi\":\"10.1007/s12039-023-02173-2\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>The catalyst Y(NO<sub>3</sub>)<sub>3</sub>, 6H<sub>2</sub>O exhibited remarkable activity in the aza-Michael addition of various aromatic and aliphatic amines with acrylonitrile at ambient temperature in a protic solvent. The method is selective for the monocyanoethylation of primary aromatic amines, aliphatic secondary amines, and sterically hindered aliphatic amines. Phenols and active methylene compounds do not undergo cyanoethylation. Thiophenol, in the presence of yttrium nitrate, promotes the polymerization of acrylonitrile. The water solubility and high catalyst stability make the process of removing the catalyst from the product easy. Direct aqueous workup of the reaction mixture could lead to the isolation of cyanoethylation products up to 99.9% purity.</p><h3>Graphical Abstract</h3>\\n <ul>\\n <li>\\n <p>Selective <i>mono-</i>cyanoethylation at the primary aromatic amine, especially electron-rich aromatic amines</p>\\n </li>\\n <li>\\n <p>Excellent regio-selectivity in the presence of Carbon and Oxygen nucleophiles</p>\\n </li>\\n <li>\\n <p>The reported condition could be used to polymerize acrylonitrile in the presence of thiophenol.</p>\\n </li>\\n <li>\\n <p>Reaction is facile for electron-rich aromatic amine.</p>\\n </li>\\n <li>\\n <p>Highly sensitive to the steric effect at the nitrogen center</p>\\n </li>\\n </ul>\\n <figure><div><div><div><picture><img></picture></div></div></div></figure>\\n </div>\",\"PeriodicalId\":50242,\"journal\":{\"name\":\"Journal of Chemical Sciences\",\"volume\":\"135 3\",\"pages\":\"\"},\"PeriodicalIF\":1.7000,\"publicationDate\":\"2023-06-12\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Chemical Sciences\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s12039-023-02173-2\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"Chemistry\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Chemical Sciences","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s12039-023-02173-2","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"Chemistry","Score":null,"Total":0}
Yttrium nitrate promoted selective cyanoethylation of amines
The catalyst Y(NO3)3, 6H2O exhibited remarkable activity in the aza-Michael addition of various aromatic and aliphatic amines with acrylonitrile at ambient temperature in a protic solvent. The method is selective for the monocyanoethylation of primary aromatic amines, aliphatic secondary amines, and sterically hindered aliphatic amines. Phenols and active methylene compounds do not undergo cyanoethylation. Thiophenol, in the presence of yttrium nitrate, promotes the polymerization of acrylonitrile. The water solubility and high catalyst stability make the process of removing the catalyst from the product easy. Direct aqueous workup of the reaction mixture could lead to the isolation of cyanoethylation products up to 99.9% purity.
Graphical Abstract
Selective mono-cyanoethylation at the primary aromatic amine, especially electron-rich aromatic amines
Excellent regio-selectivity in the presence of Carbon and Oxygen nucleophiles
The reported condition could be used to polymerize acrylonitrile in the presence of thiophenol.
Reaction is facile for electron-rich aromatic amine.
Highly sensitive to the steric effect at the nitrogen center
期刊介绍：
Journal of Chemical Sciences is a monthly journal published by the Indian Academy of Sciences. It formed part of the original Proceedings of the Indian Academy of Sciences – Part A, started by the Nobel Laureate Prof C V Raman in 1934, that was split in 1978 into three separate journals. It was renamed as Journal of Chemical Sciences in 2004. The journal publishes original research articles and rapid communications, covering all areas of chemical sciences. A significant feature of the journal is its special issues, brought out from time to time, devoted to conference symposia/proceedings in frontier areas of the subject, held not only in India but also in other countries.
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