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Biomimetic Nitration of Phenols Using Metalloporphyrins/H2O2/NO2 −

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Abstract

An efficient metalloporphyrins/H2O2/NO2 − nitration of phenols has been developed. The total yield of nitrophenol could reach up to 55.1 %, which is about 4 and sixfold higher than that of horse radish peroxidase catalysis and peroxynitrite nitration, respectively. Furthermore, the nitration system attained an enhanced regioselectivity of 1.0 o/p ratio, and exhibited a good substrate scope of monophenols. This protocol is environmentally friendly compared with HNO3/H2SO4 nitration, and stable, inexpensive and organic solvent tolerant compared with enzyme catalytic nitration and peroxynitrite nitration reaction.

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Acknowledgments

This work was supported by Key Program of the Chinese Academy of Sciences (KGZD-EW-606-1-3) and Taishan Scholars Climbing Program of Shandong (No. tspd20150210).

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Authors and Affiliations

  1. CAS Key Laboratory of Biobased Materials, Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao, 266101, China

    Weizhi Sun, Yaojie Liu, Haibo Zhang, Mo Xian & Huizhou Liu

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  1. Weizhi Sun
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  2. Yaojie Liu
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  3. Haibo Zhang
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  4. Mo Xian
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  5. Huizhou Liu
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Corresponding authors

Correspondence to Mo Xian or Huizhou Liu.

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Sun, W., Liu, Y., Zhang, H. et al. Biomimetic Nitration of Phenols Using Metalloporphyrins/H2O2/NO2 − . Catal Lett 145, 1991–1999 (2015). https://doi.org/10.1007/s10562-015-1610-8

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  • DOI: https://doi.org/10.1007/s10562-015-1610-8

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