Key Laboratory of Sensor Analysis of Tumor Marker, Ministry of Education, Shandong Key Laboratory of Biochemical Analysis, Key Laboratory of Analytical Chemistry for Life Science in Universities of Shandong, College of Chemistry and Molecular Engineering. Qingdao University of Science and Technology, Qingdao 266042, P. R. China.
Chem Commun (Camb). 2020 Sep 16;56(72):10489-10492. doi: 10.1039/d0cc04831c. Epub 2020 Aug 7.
A base-mediated cascade amidination/N-alkylation reaction of amines by alcohols has been developed. For the first time, nitriles have been identified as an efficient and benign water acceptor reagent in N-alkylation. Notably, the procedure tolerates a series of functional groups, such as methoxyl, halo, vinyl and hetero groups, providing a convenient method to construct different substituted diamino compounds, N labeled amine and could be scaled up to 1 mol scale offering 138.7 g of the desired product in good yield in one-pot. Mechanistic studies provided strong evidence for the amidination of amines with nitriles facilitated by t-BuOK.
已开发出一种基于碱介导的酰胺化/胺的 N-烷基化级联反应。首次发现腈是 N-烷基化中一种有效且温和的水接受试剂。值得注意的是，该方法可耐受一系列官能团，如甲氧基、卤素、乙烯基和杂环，为构建不同取代的二氨基化合物、N 标记的胺提供了一种方便的方法，并且可以放大到 1 摩尔规模，一锅法可提供 138.7 g 目标产物，产率良好。机理研究为叔丁醇钾促进的腈与胺的酰胺化提供了有力证据。
