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硅氢化合物辅助由一氧化碳和胺合成尿素衍生物

Hydrosilane-Assisted Synthesis of Urea Derivatives from CO and Amines.

作者信息

Zhao Yulei, Guo Xuqiang, Si Zhiyao, Hu Yanan, Sun Ying, Liu Yunlin, Ji Zhongyin, You Jinmao

机构信息

School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, China.

School of Chemistry and Chemical Engineering, Guangzhou University, Guangzhou 510006, China.

出版信息

J Org Chem. 2020 Oct 16;85(20):13347-13353. doi: 10.1021/acs.joc.0c02032. Epub 2020 Sep 30.

Abstract

A methodology employing CO, amines, and phenylsilane was discussed to access aryl- or alkyl-substituted urea derivatives. This procedure was characterized by adopting hydrosilane to promote the formation of ureas directly, without the need to prepare silylamines in advance. Control reactions suggested that FeCl was a favorable additive for the generation of ureas, and this 1,5,7-triazabicyclo[4.4.0]dec-5-ene-catalyzed reaction might proceed through nucleophilic addition, silicon migration, and the subsequent formal substitution of silylcarbamate.

摘要

讨论了一种使用一氧化碳、胺类和苯基硅烷来制备芳基或烷基取代脲衍生物的方法。该方法的特点是采用硅烷直接促进脲的形成,无需预先制备硅胺。对照反应表明,氯化铁是生成脲的有利添加剂,并且这种由1,5,7-三氮杂双环[4.4.0]癸-5-烯催化的反应可能通过亲核加成、硅迁移以及随后甲硅烷基氨基甲酸酯的形式取代来进行。

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