Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (6): 1507-1515.DOI: 10.6023/cjoc201712002 Previous Articles     Next Articles

Articles

1,5-溴三氯甲基化产物及三取代苯乙烯的E-Z异构化

李进, 陈靖之, 黄文浩, 程旭   

  1. 南京大学化学化工学院 南京 210023
  • 收稿日期:2017-12-02 修回日期:2018-01-30 出版日期:2018-06-25 发布日期:2018-02-06
  • 通讯作者: 程旭,E-mail:chengxu@nju.edu.cn E-mail:chengxu@nju.edu.cn
  • 基金资助:

    国家自然科学基金(No.21572099,21332005)资助项目.

E-Z Isomerization of 1, 5-Bromotrichloromethylation Reaction Products and Trisubstituted Styrenes

Li Jin, Chen Jingzhi, Huang Wenhao, Cheng Xu   

  1. School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023
  • Received:2017-12-02 Revised:2018-01-30 Online:2018-06-25 Published:2018-02-06
  • Contact: 10.6023/cjoc201712002 E-mail:chengxu@nju.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21572099, 21332005).

1,5-Bromotrichloromethylation of α-cyclopropylstyrenes via a radical chain pathway was achieved with Ir[dF(CF3)ppy]2(dtbbpy)PF6 as a photoinitiator under visible-light irradiation to give trisubstituted styrenes with Z/E ratio of 30:70. When the reaction mixture was further irradiated, the Z/E ratio could be reversed and increased to 99:1, probably via an energy-transfer pathway involving the Ir photocatalyst. This visible-light-induced catalytic isomerization protocol could also be applied to trisubstituted styrenes to obtain products with Z/E ratios up to 99:1.

Key words: photochemistry, radical, alkene, isomerization