Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (12): 3713-3719.DOI: 10.6023/cjoc202405051 Previous Articles     Next Articles

ARTICLE

铜介导sp3-C—N键断裂合成(二芳基甲基)二芳基膦氧化物

董建玉a,,*(), 霍杰a,b,, 郭莹b, 周丹b, 周永波b,*()   

  1. a 湖南第一师范学院物理与化学学院 长沙 410205
    b 湖南大学化学化工学院 教育部先进催化工程研究中心 长沙 410082
  • 收稿日期:2024-05-31 修回日期:2024-09-05 发布日期:2024-09-18
  • 作者简介:
    †共同第一作者.
  • 基金资助:
    国家自然科学基金(22378106); 国家自然科学基金(21706058); 国家自然科学基金(21878072); 国家自然科学基金(22002169); 湖南省自然科学基金(2020JJ2011); 中国博士后科学基金(2019M662774)

Copper Mediated sp3-C—N Bond Cleavage for Synthesizing (Diarylmethyl)diarylphosphine Oxides

Jianyu Donga,,*(), Jie Huoa,b,, Ying Guob, Dan Zhoub, Yongbo Zhoub,*()   

  1. a School of Physics and Chemistry, Hunan First Normal University, Changsha 410205
    b Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082
  • Received:2024-05-31 Revised:2024-09-05 Published:2024-09-18
  • Contact: *E-mail:djyustc@hotmail.com;zhouyb@hnu.edu.cn
  • About author:
    †The authors contributed equally to this work.
  • Supported by:
    National Natural Science Foundation of China(22378106); National Natural Science Foundation of China(21706058); National Natural Science Foundation of China(21878072); National Natural Science Foundation of China(22002169); Natural Science Foundation of Hunan Province(2020JJ2011); China Postdoctoral Science Foundation(2019M662774)

Organic phosphorus compounds containing sp3-CP(O) bonds are increasingly widely applied in catalysis, pharmaceuticals, materials, pesticides, and other fields, and their synthesis has become a research hotspot in chemistry. Diarylmethyl phosphine oxides are important organic phosphorus compounds containing sp3-CP(O) bonds, but their synthesis is limited. Traditional methods for their synthesis require the use of halogenated compounds and harsh reaction conditions. A new method for the copper-mediated synthesis of (diarylmethyl)diarylphosphine oxides has been developed. This method involves the cleavage of the sp3-CN bond in N-diarylmethylsulfonamides, leading to the formation of diarylmethyl carbocations. The carbocations then react with diarylphosphine oxides to construct sp3-CP(O) bonds. Our method only requires the addition of stoichiometric, inexpensive CuBr2 and produces a series of target compounds in satisfactory yields. Thus, it provides a convenient, and cost-effective pathway for the synthesis of diarylmethyl phosphine oxides.

Key words: copper mediated reaction, sp3-C—N bond cleavage, sp3-C—P(O) bond formation, diarylmethylphosphine oxides