高等学校化学学报 ›› 2011, Vol. 32 ›› Issue (12): 2782.

• 研究论文 • 上一篇    下一篇

烯酸在有机高价碘试剂催化下的氯代内酯化反应

方应国,  徐翠,  朱敏   

  1. 浙江树人大学生物与环境工程学院,  杭州 310015
  • 收稿日期:2011-01-19 修回日期:2011-03-20 出版日期:2011-12-10 发布日期:2011-11-25
  • 通讯作者: 朱敏 E-mail:hzzm60@163.com
  • 基金资助:

    国家自然科学基金(批准号: 21072176)和浙江省自然科学基金(批准号: Y4100231)资助.

Catalysis of Chlorolactonization of Pentenoic Acids with Hypervalent Iodine(Ⅲ) Reagent

FANG Ying-Guo, XU Cui, ZHU Min*   

  1. College of Biological and Environmental Sciences, Zhejiang Shuren University, Hangzhou 310015, China
  • Received:2011-01-19 Revised:2011-03-20 Online:2011-12-10 Published:2011-11-25
  • Contact: ZHU Min E-mail:hzzm60@163.com
  • Supported by:

    国家自然科学基金(批准号: 21072176)和浙江省自然科学基金(批准号: Y4100231)资助.

摘要: 研究了不饱和烯酸在有机高价碘催化剂和间氯过氧苯甲酸作用下与氯化锂的反应.  通过该反应,  4-戊烯酸等可在常温下短时间内得到良好产率的氯代γ-丁内酯化合物, 提供了简单快速合成氯代γ-丁内酯的新方法. 考察了反应条件的影响,  并提出了可能的反应机理.  

关键词: 有机高价碘试剂; , 催化内酯化反应; , 4-戊烯酸; , 合成

Abstract: Recently, the catalytic utilization of hypervalent iodine reagents is increasing in importance, with the growing interest in the development of environmentally benign synthetic transformations.  Halolactonization has been studied extensively, and this type of transformation serves as an important key reaction in a variety of syntheses.  However, compared with iodolactonization and bromolactonization, there are relatively few examples of chlorolactonization.  In order to improve the chlorolactonization, the cyclization of alkenoic acids under catalyst PhI was  investigated, a novel and convenient catalytic method for chlorolactonization of pentenoic acids was  developed.  In this protocol, 4-pentenoic acids reacted with lithium chloride fast under catalyst iodobenzene in combination with m-chloroperbenzoic acid as the terminal oxidant in CH2Cl2 at room temperature, which provided  five-membered chlorolactones in good yields. This method has some advantages such as mild reaction conditions, simple procedure and good yields. Furthermore, the scope of hypervalent iodine reagents in organic synthesis could be extended.

Key words: Hypervalent iodine reagent, Catalytic chlorolactonization, 4-Pentenoic acid, Synthesis

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