有机化学 ›› 2019, Vol. 39 ›› Issue (6): 1672-1680.DOI: 10.6023/cjoc201903054 上一篇    下一篇

所属专题: 金属有机化学

研究论文

通过锌催化区域选择性氧化反应实现3-烯-1-炔的1,4-官能团化

郑人华a, 郭海昌a, 阳明洋b, 刘梦琪b, 叶龙武b   

  1. a 台州学院医药化工与材料工程学院 台州 318000;
    b 厦门大学化学化工学院 厦门 361005
  • 收稿日期:2019-03-25 修回日期:2019-04-24 出版日期:2019-06-25 发布日期:2019-05-06
  • 通讯作者: 郑人华, 叶龙武 E-mail:zhengrh@tzc.edu.cn;longwuye@xmu.edu.cn
  • 基金资助:

    浙江省公益技术应用研究计划(No.LGG19B040001)、台州市科技计划(No.1801gy21)、国家自然科学基金(Nos.21572186,21622204)和教育部创新团队资助项目.

1,4-Functionalization of 3-En-1-ynes with Alcohols via Zinc-Catalyzed Regioselective N-Oxide Oxidation

Zheng Renhuaa, Guo Haichanga, Yang Mingyangb, Liu Mengqib, Ye Longwub   

  1. a School of Pharmaceutical and Materials Engineering, Taizhou University, Taizhou 318000;
    b College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005
  • Received:2019-03-25 Revised:2019-04-24 Online:2019-06-25 Published:2019-05-06
  • Contact: 10.6023/cjoc201903054 E-mail:zhengrh@tzc.edu.cn;longwuye@xmu.edu.cn
  • Supported by:

    Project supported by the Zhejiang Provincal Public Welfare Technology Research Program (No. LGG19B040001), the Taizhou Science and Technology Project (No. 1801gy21), the National Natural Science Foundation of China (Nos. 21572186, 21622204) and the Program for Changjiang Scholars and Innovative Research Team in University (PCSIRT).

γ-羟基或烷氧基取代的α,β-不饱和羰基化合物广泛存在于众多天然产物和生物活性分子之中.通过锌催化的区域选择性的氮氧化合物氧化炔烃反应,实现了3-烯-1-炔的4-烷氧化-1-氧化官能团化.该串联反应可以中等到良好的产率得到系列合成上很有用的γ-烷氧基取代的α,β-不饱和酰胺化合物.

关键词: 氧化反应, 1,4-官能团化, 炔烃, 串联反应

γ-Hydroxyl or γ-alkoxyl-substituted α,β-unsaturated carbonyls widely exist in a variety of natural products and bioactive molecules. Herein, the realization of 1,4-functionalization of 3-en-1-ynes with alcohols through zinc-catalyzed regioselective N-oxide oxidation is described. This tandem reaction allows the practical synthesis of a range of valuable γ-alkoxyl-substituted-α,β-unsaturated amides in moderate to good yields.

Key words: oxidation, 1,4-functionalization, alkynes, tandem reaction