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Cs2CO3-Promoted One-Pot Synthesis of Alkynylphosphonates, -phosphinates, and -phosphine Oxides

  • Yulei Wang
    Yulei Wang
    Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, China
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  • , 
  • Jiepeng Gan
    Jiepeng Gan
    Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, China
    More by Jiepeng Gan
  • , 
  • Liu Leo Liu
    Liu Leo Liu
    Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, China
    More by Liu Leo Liu
  • , 
  • Hang Yuan
    Hang Yuan
    Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, China
    More by Hang Yuan
  • , 
  • Yuxing Gao*
    Yuxing Gao
    Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, China
    *E-mail: [email protected]
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  • , 
  • Yan Liu*
    Yan Liu
    Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, China
    *E-mail: [email protected]
    More by Yan Liu
  • , and 
  • Yufen Zhao
    Yufen Zhao
    Department of Chemistry, College of Chemistry and Chemical Engineering, and the Key Laboratory for Chemical Biology of Fujian Province  and  Department of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China
    More by Yufen Zhao
Cite this: J. Org. Chem. 2014, 79, 8, 3678–3683
Publication Date (Web):March 24, 2014
https://doi.org/10.1021/jo500312n
Copyright © 2014 American Chemical Society
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    Abstract

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    A novel and efficient Cs2CO3-promoted phosphorylation or phosphinylation of various 1,1-dibromo-1-alkenes with readily available trialkyl phosphites, ethyl diphenylphosphinite, or diethyl phenylphosphonite has been developed under metal-free conditions, providing a practical and powerful tool for one-pot synthesis of valuable alkynylphosphonates, -phosphinates, and -phosphine oxides in good to excellent yields.

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    39. Xiang Li, Suyan Sun, Fan Yang, Jianxun Kang, Yusheng Wu, Yangjie Wu. Palladium-catalyzed oxidative deacetonative coupling of 4-aryl-2-methyl-3-butyn-2-ols with H-phosphonates. Organic & Biomolecular Chemistry 2015, 13 (8) , 2432-2436. https://doi.org/10.1039/C4OB02410A
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    41. Yulei Wang, Jiepeng Gan, Liu Liu, Hang Yuan, Yuxing Gao, Yan Liu, Yufen Zhao. ChemInform Abstract: Cs 2 CO 3 -Promoted One-Pot Synthesis of Alkynylphosphonates, -phosphinates, and -phosphine Oxides.. ChemInform 2014, 45 (45) , no-no. https://doi.org/10.1002/chin.201445207
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