Ramanathan Mani, Wang Yu-Hao, Liu Yi-Hung, Peng Shie-Ming, Cheng Yuan-Chung, Liu Shiuh-Tzung
Department of Chemistry , National Taiwan University , Taipei 106 , Taiwan.
J Org Chem. 2018 Jun 1;83(11):6133-6141. doi: 10.1021/acs.joc.8b01000. Epub 2018 May 10.
A transition-metal-free approach for the preparation of N-arylketimines has been developed from the direct reaction of aryldiazonium salts, arenes, and nitriles in a one-pot fashion with the consecutive formation of N-C and C-C bonds. This approach proceeds via an in situ generation of N-arylnitrilium intermediate, which then undergoes intermolecular arylation. This three-component strategy offers a step- and atom-efficient way to N-arylketimines from easily accessible reagents under mild reaction conditions. The characterization of stereochemistry of ketimine was achieved by X-ray crystallographic structure and theoretical calculation. Operational simplicity, shorter reaction time, excellent functional group compatibility, and scalability are the key features of this report.
已开发出一种无过渡金属的方法来制备N-芳基酮亚胺，该方法是通过芳基重氮盐、芳烃和腈的一锅法直接反应，依次形成N-C键和C-C键。该方法通过原位生成N-芳基腈鎓中间体进行，然后该中间体进行分子间芳基化反应。这种三组分策略提供了一种步骤和原子经济高效的方法，可在温和的反应条件下，从易于获得的试剂制备N-芳基酮亚胺。通过X射线晶体结构和理论计算实现了酮亚胺立体化学的表征。操作简便、反应时间短、优异的官能团兼容性和可扩展性是本报告的关键特征。
