金催化联烯胺与烯基叠氮的加成反应构建α-烯丙基酮化合物
Synthesis of α-allyl ketones via gold-catalyzed coupling of allenamides with vinyl azides
杨岚 1古文 1王甜密 1李肖肖 1赵志刚1
作者信息
- 1. 西南民族大学化学与环境学院,四川 成都 610041
- 折叠
摘要
烯基叠氮是一类重要的有机合成中间体,被广泛应用于含氮杂环化合物的合成中,但将其应用于联烯胺的加成反应少见报道.利用金催化活化联烯胺形成的烯丙基正离子中间体与烯丙基叠氮化合物发生加成反应,进一步发生水解得到9 个α-烯丙基酮衍生物,所得产物均通过红外、核磁共振以及高分辨质谱进行确认,其中,对化合物3i进行了X-单晶衍射,确定了其结构.该反应利用烯基叠氮作为亲核试剂,实现了联烯胺与其加成反应,丰富了联烯胺的反应类型.
Abstract
Vinyl azides are versatile building blocks which are widely applied to the synthesis of nitrogen-containing heterocycles.However,there is no report on the coupling reaction of allenamides with vinyl azides.This paper reported an effi-cient addition reaction of vinyl azides with allyl cationic intermediate formed by gold-catalyzed activation of allenamides,which subsequently hydrolyzed to obtain 9 of α-allyl ketones.All the products were characterized by IR,NMR and HRMS.Moreover,the precise configuration of α-allyl ketones was unambiguously confirmed by single-crystal X-ray analysis of 3i.This method en-riched the study of allenamides via using vinyl azides as the nucleophilic reagents to the addition reactions of allenamides.
关键词
金催化/联烯胺/烯基叠氮/加成反应/α-烯丙基酮Key words
gold catalysis/allenamides/vinyl azides/addition reaction/α-allyl ketone引用本文复制引用
基金项目
西南民族大学中央高校基本科研业务费专项资金项目(ZYN2022017)
出版年
2024
NETL
NSTL
维普
万方数据