辽宁石油化工大学学报

辽宁石油化工大学学报 ›› 2020, Vol. 40 ›› Issue (3): 18-23.DOI: 10.3969/j.issn.1672-6952.2020.03.004

• 化学与化学工程 • 上一篇    下一篇

钯催化间甲基苯乙酸和布洛芬的间位烯基化反应

焦博杜海武戴振华王景芸   

  1. 辽宁石油化工大学 化学化工与环境学部,辽宁 抚顺 113001
  • 收稿日期:2019-04-12 修回日期:2020-03-13 出版日期:2020-06-29 发布日期:2020-07-06
  • 通讯作者: 王景芸(1980⁃),女,博士,副教授,从事碳氢键活化方面的研究;E⁃mail:jingyun.wang@lnpu.edu.cn。
  • 作者简介:焦博(1994?),男,硕士研究生,从事碳氢键活化方面的研究;E?mail:694997838@qq.com。
  • 基金资助:
    国家自然科学基金项目(21702087)。

Palladium⁃Catalyzed meta⁃Alkenylation of m⁃Methylphenylacetic Acid and Ibuprofen

Jiao BoDu HaiwuDai ZhenhuaWang Jingyun   

  1. College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Fushun Liaoning 113001, China
  • Received:2019-04-12 Revised:2020-03-13 Published:2020-06-29 Online:2020-07-06

摘要: 由于反应过程中形成不稳定的大环金属中间体和较高的过渡态内能导致反应较难进行,芳烃直接间位碳氢官能化具有很大挑战性。在过渡金属钯催化条件下,研究了嘧啶模板导向的芳基乙酸间位碳氢烯基化反应。对反应条件进行优化,考察了溶剂效应、催化剂、氧化剂的种类对反应的影响,获得最佳的反应条件。结果表明,所设计的嘧啶导向的芳基乙酸碳氢键活化反应可以实现芳基乙酸衍生物的间位高选择性官能化反应,利用该策略可构建出具有潜在药物活性的间位烯基化的布洛芬衍生物。

关键词: 钯催化剂,  间甲基苯乙酸,  布洛芬,  烯基化,  嘧啶模板

Abstract: The direct meta⁃C-H functionalization has proved to be more challenging due to the high energy transition state of marcrocyclic metallacycles which makes its formation extremely difficult. In this paper, the reaction of allyl acetic acid alkenylation based on pyrimidine template under palladium catalysis was studied. The reaction conditions were optimized, the influences of solvent effect, catalyst and oxidant type on the reaction were investigated, and the optimal reaction conditions were obtained. The experimental results show that the designed pyrimidine⁃directed aryl acetic acid C-H bond activation reaction can realize the meta⁃selective functionalization reaction of aryl acetic acid derivatives. A meta⁃alkenylation ibuprofen derivatives with potential drug activity can be constructedby using this strategy.

Key words: Palladium catalyst, m?Methylphenylacetic, Ibuprofen, Alkenylation, Pyrimidine template

引用本文

焦博, 杜海武, 戴振华, 王景芸. 钯催化间甲基苯乙酸和布洛芬的间位烯基化反应[J]. 辽宁石油化工大学学报, 2020, 40(3): 18-23.

Jiao Bo, Du Haiwu, Dai Zhenhua, Wang Jingyun. Palladium⁃Catalyzed meta⁃Alkenylation of m⁃Methylphenylacetic Acid and Ibuprofen[J]. Journal of Liaoning Petrochemical University, 2020, 40(3): 18-23.

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链接本文: https://journal.lnpu.edu.cn/CN/10.3969/j.issn.1672-6952.2020.03.004

               https://journal.lnpu.edu.cn/CN/Y2020/V40/I3/18