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Chinese Journal of Organic Chemistry >

2014 , Vol. 34 >Issue 7: 1340 - 1346

DOI: https://doi.org/10.6023/cjoc201403048

ARTICLE

Copper-Catalyzed Aerobic Oxidative C-P Coupling of Arylboronic Acids and Diethyl Phosphite under Air

  • Xu Qing ,
  • Jia Xiaojuan ,
  • Li Xiaohui ,
  • Sun Qing ,
  • Zhou Yongbo ,
  • Yin Shuangfeng ,
  • Han Libiao
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  • a College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035;
    b College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
    c National Institute of Advanced Industrial Science and TechnologyAIST), Tsukuba, Ibaraki 305-8565, Japan

Received date: 2014-03-23

  Revised date: 2014-05-10

  Online published: 2014-05-23

Supported by

Project supported by the National Natural Science Foundation of China (No. 20902070) and the Natural Science Foundation of Zhejiang Province for Distinguished Young Scholars (No. LR14B020002).

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Abstract

By using Cu(OAc)2/TMEDA as the catalyst and air as the direct oxidant, arylboronic acids and diethyl phosphite can readily undergo an aerobic oxidative C-P coupling reaction under air at room temperature to give the useful arylphosphonates. This reaction uses relatively cheaper and less toxic copper salts as the catalyst, tolerates moisture and aerobic conditions. is suitable for a comparatively broad scope of substrates, and can give the target arylphosphonates in high selectivities and good yields. In comparison with conventional metal-catalyzed C-P coupling reactions of aryl halides, it is a relatively mild and efficient method for the synthesis of arylphosphonates.

Key words： copper catalysis; arylboronic acids; diethyl phosphite; oxidative coupling; C-P bond construction; arylphosphonates

Cite this article

Xu Qing , Jia Xiaojuan , Li Xiaohui , Sun Qing , Zhou Yongbo , Yin Shuangfeng , Han Libiao . Copper-Catalyzed Aerobic Oxidative C-P Coupling of Arylboronic Acids and Diethyl Phosphite under Air[J]. Chinese Journal of Organic Chemistry, 2014 , 34(7) : 1340 -1346 . DOI: 10.6023/cjoc201403048

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