高等学校化学学报 ›› 2019, Vol. 40 ›› Issue (5): 927-931.doi: 10.7503/cjcu20180540

• 有机化学 • 上一篇    下一篇

硫酸铜/取代硫脲水相中高效催化合成N-磺酰基三氮唑

董丽蓉1, 王思雨1, 张小媚1, 成佳佳1, 袁耀锋1,2()   

  1. 1. 福州大学化学学院, 福州 350116
    2. 中国科学院福建物质结构研究所结构化学国家重点实验室, 福州 350002
  • 收稿日期:2018-07-30 出版日期:2019-03-29 发布日期:2019-03-29
  • 作者简介:

    联系人简介: 袁耀锋, 男, 博士, 教授, 博士生导师, 主要从事功能有机分子的设计合成与性能研究. E-mail: yaofeng_yuan@fzu.edu.cn

  • 基金资助:
    国家自然科学基金(批准号: 21772023)、 福建省科技计划项目(批准号: 2015H6010)和中国科学院福建物质结构研究所结构化学国家重点实验室项目(批准号: 20180020)资助.

High Efficiency Catalytic Synthesis of N-Sulfonyltriazole in Aqueous Phase by Copper Sulfate/Substituted Thiourea

DONG Lirong1, WANG Siyu1, ZHANG Xiaomei1, CHENG Jiajia1, YUAN Yaofeng1,2,*()   

  1. 1. College of Chemistry, Fuzhou University, Fuzhou 350116, China
    2. State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China
  • Received:2018-07-30 Online:2019-03-29 Published:2019-03-29
  • Contact: YUAN Yaofeng E-mail:yaofeng_yuan@fzu.edu.cn
  • Supported by:
    † Support by the National Natural Science Foundation of China(No.21772023), the Fujian Province Project of Science and Technology, China(No.2015H6010) and the Research Fund for the State Key Laboratory of Structural Chemistry, the Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, China(No.20180020)

摘要:

利用系列含磺酰基的叠氮化物与末端炔反应, 制备了N-磺酰基三氮唑化合物. 研究结果表明, 硫酸铜/取代硫脲的组合不仅适用于一般的铜催化叠氮端炔环加成(CuAAC)反应, 还可以在水相中高效催化合成N-磺酰基-1,2,3-三氮唑. 这类反应对水不敏感, 在水相中的反应产率高达99%, 且在空气中室温(25 ℃)下搅拌即可进行. 该方法反应条件温和、 绿色环保、 成本低、 底物普适性广且反应效率高.

关键词: 叠氮化物, 铜催化叠氮端炔环加成反应, 水相, N-磺酰基三氮唑

Abstract:

The reaction of a series of sulfonyl-containing azides and terminal alkynes indicated that the combination of copper sulfate/substituted thiourea was more suitable for general copper-catalyzed azide-end alkyne ring addition[Cu(Ⅰ) catalyzed azide-alkyne cycloaddition, CuAAC] reaction. The type of reaction was also possible to efficiently catalyze the synthesis of N-sulfonyl-1,2,3-triazole in the aqueous phase. The type of reaction was not sensitive to water and the yield was up to 99% in the aqueous phase. The reaction mixture was stirred in the air under room temperature(25 ℃). The novel system showed high atom-economy and functional-group tolurance. It provided a simple and efficient synthesis method for the synthesis of a series of N-sulfonyltriazoles.

Key words: Azide, Cu(Ⅰ) catalyzed axide-alhyne cycloaddition(CuAAC) reaction;, Aqueous phase, N-Sulfonyltriazole

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