Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (7): 2098-2105.DOI: 10.6023/cjoc202203020 Previous Articles     Next Articles

Special Issue: 有机氟化学虚拟合辑

ARTICLES

钯催化的氯二氟乙基高价碘试剂对于乙酰苯胺C—H键的氯二氟乙基化反应研究

曹成瑶a, 牛亚茹b, 蒋昀辰a, 曲红梅b, 陈超a,c,*()   

  1. a清华大学化学系 生物有机磷化学与化学生物学教育部重点实验室 北京 100084
    b天津大学化工学院制药工程系 系统生物工程教育部重点实验室 天津 300350
    c南开大学 元素有机化学国家重点实验室 天津 300071
  • 收稿日期:2022-03-10 修回日期:2022-04-08 发布日期:2022-08-09
  • 通讯作者: 陈超
  • 基金资助:
    国家重点研发项目(2016YFB0401400); 国家自然科学基金(22071129); 国家自然科学基金(21871158); 国家自然科学基金(21672120); 霍英东基金(151014)

Pd-Catalyzed Chlorodifluoroethylation Reaction of C—H Bond of Acetanilides with Chlorodifluoroethyl Iodonium Reagents

Chengyao Kimmy Caoa, Yaru Niub, Yunchen Jianga, Hongmei Qub, Chao Chena,c()   

  1. aKey Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084
    bKey Laboratory of Systems Bioengineering, Ministry of Education, Department of Pharmaceutical Engineering, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300350
    cState Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071
  • Received:2022-03-10 Revised:2022-04-08 Published:2022-08-09
  • Contact: Chao Chen
  • Supported by:
    National Key Research and Development Program of China(2016YFB0401400); National Natural Science Foundation of China(22071129); National Natural Science Foundation of China(21871158); the National Natural Science Foundation of China(21672120); Fok Ying Tong Education Foundation of China(151014)

Difluoroethyl products have a wide range of applications in the fields of biomedicine and materials, and it is important to develop new method to synthesize difluoroethyl compounds. Herein, a palladium-catalyzed chlorodifluoroethylation was disclosed via ortho-C—H activation of acetanilide, using chlorodifluoroethyl(mesityl) hypervalent iodine reagent as the source of CH2CF2Cl. Moreover, adding organic base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to the above system, the difluorovinylated acetanilide products were obtained via an elimination reaction.

Key words: C—H activation, palladium catalyzed, acetanilide, iodonium salts, chlorodifluoroethylation, difluorovinylation