四丁基碘化胺催化活化烯烃烷氧羰基化反应:合成异喹啉二酮衍生物

doi:10.6023/cjoc201410015

有机化学 ›› 2015, Vol. 35 ›› Issue (4): 875-881.DOI: 10.6023/cjoc201410015 上一篇下一篇

研究论文

四丁基碘化胺催化活化烯烃烷氧羰基化反应:合成异喹啉二酮衍生物

唐裕才, 张敏, 李小青, 许响生, 杜晓华

浙江工业大学化学工程学院杭州 310014

收稿日期:2014-10-11 修回日期:2014-11-19 发布日期:2014-12-02
通讯作者: 杜晓华 E-mail:duxiaohua@zjut.edu.cn
基金资助:
国家自然科学基金(No. 21102130)和浙江省科技创新团队(Nos. 2010R50018, 2011R50017)资助项目.

Tetrabutylammonium Iodide-Catalyzed Radical Alkoxycarbonylation of Activated Alkenes: Synthesis of Isoquinolinedione Derivatives

Tang Yucai, Zhang Min, Li Xiaoqing, Xu Xiangsheng, Du Xiaohua

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Received:2014-10-11 Revised:2014-11-19 Published:2014-12-02
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21102130) and the Key Innovation Team of Science & Technology in Zhejiang Province (Nos. 2010R50018, 2011R50017).

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摘要/Abstract

异喹啉二酮骨架是一种重要的有机合成砌块, 广泛存在于生物碱、天然产物和药物中. 提供了一种非金属催化构建异喹啉二酮骨架结构的新方法. 机理研究表明, 该反应经历了一个自由基过程: 在四丁基碘化胺催化作用下, 肼化合物质子被逐步攫取生成烷氧羰基自由基, 随后对活化烯烃进行自由基加成反应, 进一步环化形成异喹啉二酮骨架. 该方法具有反应条件温和、底物普适性广、环境友好等特点, 为合成含异喹啉二酮骨架分子结构提供了一种新途径.

关键词: 异喹啉二酮结构, 非金属催化, 四丁基碘化胺, 自由基加成/环化

The isoquinolinedione skeletons are important building blocks, which have been widely present in plant alkaloids, natural products and pharmaceuticals. In this paper, a novel method to construct isoquinolinedione framework was developed, which can be easily operated under metal-free conditions. In the presence of tetrabutylammonium-iodide catalyst, hydrogen atoms were abstracted step by step from carbazate to generate methoxycarbonyl radical which followed by radical addition/cyclization reaction leading to isoquinolinedione. The presented methodology will provide new strategies for construct isoquinolinedione-type products, which has advantages of simple operation, mild reaction conditions, and environmentally benign.

Key words: isoquinolinedione skeleton, metal-free, tetrabutylammonium-iodide, radical addition/cyclization

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唐裕才, 张敏, 李小青, 许响生, 杜晓华. 四丁基碘化胺催化活化烯烃烷氧羰基化反应:合成异喹啉二酮衍生物[J]. 有机化学, 2015, 35(4): 875-881.

Tang Yucai, Zhang Min, Li Xiaoqing, Xu Xiangsheng, Du Xiaohua. Tetrabutylammonium Iodide-Catalyzed Radical Alkoxycarbonylation of Activated Alkenes: Synthesis of Isoquinolinedione Derivatives[J]. Chin. J. Org. Chem., 2015, 35(4): 875-881.

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四丁基碘化胺催化活化烯烃烷氧羰基化反应:合成异喹啉二酮衍生物

Tetrabutylammonium Iodide-Catalyzed Radical Alkoxycarbonylation of Activated Alkenes: Synthesis of Isoquinolinedione Derivatives

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