有机化学 ›› 2020, Vol. 40 ›› Issue (11): 3837-3846.DOI: 10.6023/cjoc202006043 上一篇    下一篇

研究论文

铁卟啉类化合物催化乙烯基硫醚和重氮化合物间的环丙烷化和C—S键断裂的竞争反应

闫晓静a, 李畅b, 靳智雄a, 徐孝菲a, 陈维伟a, 潘远江a   

  1. a 浙江大学化学系 杭州 310027;
    b 浙江中医药大学生命科学学院 杭州 310053
  • 收稿日期:2020-06-21 修回日期:2020-08-09 发布日期:2020-08-19
  • 通讯作者: 潘远江, 李畅 E-mail:panyuanjiang@zju.edu.cn;lichang@zju.edu.cn
  • 基金资助:
    国家科学自然基金(Nos.21532005,21502168)和国家重点研发(No.2016YFF0200503)资助项目.

Iron Porphyrin Complexes Catalyzed Cyclopropanation Reactions and C-S Bond Cleavage Reactions for Phenyl Vinyl Sulfides and Diazoreagents

Yan Xiaojinga, Li Changb, Jin Zhixionga, Xu Xiaofeia, Chen Weiweia, Pan Yuanjianga   

  1. a Departement of Chemistry, Zhejiang University, Hangzhou 310027;
    b College of Life Science, Zhejiang Chinese Medical University, Hangzhou 310053
  • Received:2020-06-21 Revised:2020-08-09 Published:2020-08-19
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21532005, 21502168) and the National Key R&D Program of China (No. 2016YFF0200503).

建立了一种能够选择性地发生环丙烷化反应和C—S键断裂反应的催化体系.对于乙烯基苯基硫醚和重氮乙腈(通过原位策略制备)间的反应,在氯化血红素的催化作用下,可得到环丙烷化反应产物;在铁酞菁的催化作用下,则得到C—S键断裂反应产物.该反应体系无需惰性气体保护、无需高温、室温下搅拌1 h即可以中等到优秀的产率获得对应的目标产物.

关键词: 氯化血红素, 重氮化合物, 硫叶立德, 环丙烷化反应, C—S键断裂反应

A catalytic system capable of selectively promoting the cyclopropanation reaction and C—S bond cleavage reaction was established. For the reactions between phenyl vinyl sulfide and diazoacetonitrile (generated by in situ method), the cyclopropanation reaction products were obtained under the catalysis of hemin chloride, and the C—S bond cleavage reaction products were generated in the presence of FePc. All the reations were operated without inert gas protection or high temperature, and the target products were obtained by stirring at room temperature for 1 h in moderate to excellent yields.

Key words: hemin, diazo compound, sulfonium ylide, cyclopropanelation reaction, C-S bond cleavage reaction