Yttrium nitrate promoted selective cyanoethylation of amines

IF 1.7 4区化学 Q3 Chemistry

Journal of Chemical Sciences Pub Date : 2023-06-12 DOI:10.1007/s12039-023-02173-2

Arunava Misra, SK Rajibul Haque, Mohabul A Mondal

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Abstract

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

Abstract Image

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硝酸钇促进胺的选择性氰乙化

催化剂Y(NO3) 3,6h2o在常温下与丙烯腈加成各种芳香胺和脂肪胺的活性显著。该方法可选择性地对伯芳胺、脂肪族仲胺和位阻脂肪族胺进行单氰乙化反应。酚类和活性亚甲基化合物不发生氰乙基化。噻吩在硝酸钇的存在下，促进丙烯腈的聚合。催化剂的水溶性和高稳定性使得从产品中去除催化剂的过程变得容易。反应混合物的直接水处理可以分离纯度高达99.9%的氰乙化产物。伯胺选择性单氰乙基化;在碳亲核试剂和氧亲核试剂存在下具有优异的区域选择性。本文报道的条件可用于在噻吩存在下聚合丙烯腈。富电子芳香胺的反应很容易。对氮中心的位阻效应高度敏感

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来源期刊

Journal of Chemical Sciences Chemistry-General Chemistry

CiteScore

2.90

自引率

5.90%

发文量

107

审稿时长

12 months

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.