镍催化β-溴-α-氨基酸与溴化氮杂芳烃的交叉偶联反应  

Study on Migratory Cross-coupling Betweenβ-bromo-α-amino Acids and Pyridinyl Bromide with Nickel Catalysis

作　　者：张亚凤 黎樱子 刘一豪 陈妍祺 徐振华 唐石[1] ZHANG Yafeng;LI Yingzi;LIU Yihao;CHEN Yanqi;XU Zhenhua;TANG Shi(College of Chemistry and Chemical Engineering,Jishou University,Jishou 416000,China)

机构地区：[1]吉首大学化学化工学院,湖南吉首416000

出　　处：《化工技术与开发》2022年第10期16-19,26,共5页Technology & Development of Chemical Industry

摘　　要：本文探究了镍催化的氨基酸酯卤化物与氮杂芳烃溴的还原交叉偶联反应。起始原料是苄胺和苯甲醛,经胺醛缩合反应、取代反应、亲核加成反应、羟基Appel溴化反应、还原交叉偶联等反应,成功制备了2-(苄基(喹啉-3-甲基)氨基)3-苯基己酸乙酯和2-(苄基(吡啶-3-甲基)氨基)3-苯基己酸乙酯。该合成路线的起始原料价廉易得,合成方法的步骤简便,具有清洁易操作、条件温和等优点。此研究为非天然氨基酸的合成提供了新思路,扩充了氨基酸的多样性功能库,应用前景较广阔。A nickel-catalyzed reductive cross-coupling reaction between amino acid ester halide and pyridinyl bromides was studied in this paper.Applied benzylamine and benzaldehyde as start materials,ethyl 2-(benzyl(quinoline-3-methyl)amino)3-phenylcaproate and ethyl 2-(benzyl(pyridin-3-methyl)amino)3-phenylcaproate were successfully prepared through amine aldehyde condensation reaction,substitution reaction,nucleophilic addition reaction,appel bromination and reduction cross coupling.This study provided a new idea for the synthesis of unnatural amino acids and expanded the functional library of amino acid diversity.

关 键 词：镍催化 溴化氮杂芳烃 还原交叉偶联 胺醛缩合 

分 类 号：O621.3[理学—有机化学]