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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 7: 2098 - 2105

DOI: https://doi.org/10.6023/cjoc202203020

ARTICLES

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

  • Chengyao Kimmy Cao ,
  • Yaru Niu ,
  • Yunchen Jiang ,
  • Hongmei Qu ,
  • Chao Chen
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  • 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
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Received date: 2022-03-10

  Revised date: 2022-04-08

  Online published: 2022-04-22

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)

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Abstract

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

Cite this article

Chengyao Kimmy Cao , Yaru Niu , Yunchen Jiang , Hongmei Qu , Chao Chen . Pd-Catalyzed Chlorodifluoroethylation Reaction of C—H Bond of Acetanilides with Chlorodifluoroethyl Iodonium Reagents[J]. Chinese Journal of Organic Chemistry, 2022 , 42(7) : 2098 -2105 . DOI: 10.6023/cjoc202203020

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