Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 84-94.DOI: 10.6023/cjoc201808029 Previous Articles     Next Articles

Special Issue: 庆祝陈庆云院士九十华诞

Reviews

基于芳基(三氟乙基)三价碘盐的三氟乙基化反应研究进展

韩秋燕, 赵成龙, 张成潘   

  1. 武汉理工大学化学化工与生命科学学院 武汉 430070
  • 收稿日期:2018-08-25 修回日期:2018-09-19 出版日期:2019-01-25 发布日期:2018-10-20
  • 通讯作者: 张成潘 E-mail:cpzhang@whut.edu.cn,zhangchengpan1982@hotmail.com
  • 基金资助:

    国家自然科学基金(No.21602165)、湖北省“楚天学者”计划、湖北省“百人计划”资助项目.

Progress on Trifluoroethylation Reactions Using Aryl(trifluoroethyl)iodonium Salts

Han Qiuyan, Zhao Chenglong, Zhang Chengpan   

  1. School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, Wuhan 43007
  • Received:2018-08-25 Revised:2018-09-19 Online:2019-01-25 Published:2018-10-20
  • Contact: 10.6023/cjoc201808029 E-mail:cpzhang@whut.edu.cn,zhangchengpan1982@hotmail.com
  • Supported by:

    Project supported by the National Natural Science Foundation of China (21602165), the "Chutian Scholar" Program from Department of Education of Hubei Province, and the "Hundred Talent" Program of Hubei Province.

Transition metal-free and metal-catalyzed reactions using aryl(trifluoroethyl)iodonium salts as the trifluoroethylation reagents are summarized in this review. A large number of different types of N-, O-, S-, and C-nucleophiles were readily trifluoroethylated in these reactions under mild conditions. The results revealed that aryl(trifluoroethyl)iodonium salts possess much higher electrophilic reactivity than the other CH2CF3 sources. Especially, aryl(trifluoroethyl)iodonium bis(trifluoromethanesulfonyl)amides are stable and slightly soluble in water, which were successfully applied in the aqueous trifluoroethylation of amino acid derivatives and peptides. The utilization of aryl(trifluoroethyl)iodonium salts for aromatic trifluoroethylation has promisingly solved the problems that arise from the other reagents. These achievements have also demonstrated the synthetic possibilities of direct trifluoroethylation using aryl(trifluoroethyl)iodonium salts under transition-metal catalysis.

Key words: trifluoroethylation, transition metal-free, transition metal-catalyzed, electrophilic, aryl (trifluoroethyl)iodonium salts