Highly Selective 1,4- and 1,6-Addition of P(O)[BOND]H Compounds to p-Quinones: A Divergent Method for the Synthesis of C- and O-Phosphoryl Hydroquinone Derivatives

Authors

  • Biquan Xiong,

    1. Department of Chemistry, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082 (P. R. China), Fax: (+86) 731-88821310
    2. National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki 305-8565 (Japan)
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  • Ruwei Shen,

    1. State Key Laboratory of Materials-Oriented, Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing 210009 (P. R. China)
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  • Midori Goto,

    1. National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki 305-8565 (Japan)
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  • Shuang-Feng Yin,

    Corresponding author
    1. Department of Chemistry, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082 (P. R. China), Fax: (+86) 731-88821310
    • Department of Chemistry, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082 (P. R. China), Fax: (+86) 731-88821310
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  • Li-Biao Han

    Corresponding author
    1. Department of Chemistry, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082 (P. R. China), Fax: (+86) 731-88821310
    2. National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki 305-8565 (Japan)
    • Department of Chemistry, College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082 (P. R. China), Fax: (+86) 731-88821310
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Abstract

The reaction of P(O)[BOND]H compounds with p-quinones could proceed through either 1,4- or 1,6-addition pathways by employing different additives to selectively give the corresponding C- and O-phosphoryl hydroquinone derivatives in good yields. Oxidative double 1,4-addition of P(O)[BOND]H compounds to p-quinones was also achieved by tuning the solvent, affording a facile synthesis of bis-substituted hydroquinones with phosphorus functionality. Further studies on these reactions by using optically active H-phosphinates showed that all addition reactions took place stereospecifically with retention of configuration at the phosphorus center. The findings lead to the establishment of a divergent method for the synthesis of C- and O-phosphoryl hydroquinone derivatives from easily available P(O)[BOND]H compounds.

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