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A redox-neutral catechol synthesis

Author

Listed:
  • Qian Wu

    (Guangdong Key Lab of Nano-Micro Material Research, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School)

  • Dingyuan Yan

    (State Key Laboratory of Coordination Chemistry, Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Collaborative Innovation Centre of Chemistry for Life Sciences, Nanjing University)

  • Ying Chen

    (Guangdong Key Lab of Nano-Micro Material Research, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School)

  • Ting Wang

    (School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School)

  • Feng Xiong

    (State Key Laboratory of Coordination Chemistry, Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Collaborative Innovation Centre of Chemistry for Life Sciences, Nanjing University)

  • Wei Wei

    (State Key Laboratory of Coordination Chemistry, Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Collaborative Innovation Centre of Chemistry for Life Sciences, Nanjing University)

  • Yi Lu

    (State Key Laboratory of Coordination Chemistry, Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Collaborative Innovation Centre of Chemistry for Life Sciences, Nanjing University)

  • Wei-Yin Sun

    (State Key Laboratory of Coordination Chemistry, Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Collaborative Innovation Centre of Chemistry for Life Sciences, Nanjing University)

  • Jie Jack Li

    (University of San Francisco)

  • Jing Zhao

    (Guangdong Key Lab of Nano-Micro Material Research, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School
    State Key Laboratory of Coordination Chemistry, Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Collaborative Innovation Centre of Chemistry for Life Sciences, Nanjing University)

Abstract

Ubiquitous tyrosinase catalyses the aerobic oxidation of phenols to catechols through the binuclear copper centres. Here, inspired by the Fischer indole synthesis, we report an iridium-catalysed tyrosinase-like approach to catechols, employing an oxyacetamide-directed C–H hydroxylation on phenols. This method achieves one-step, redox-neutral synthesis of catechols with diverse substituent groups under mild conditions. Mechanistic studies confirm that the directing group (DG) oxyacetamide acts as the oxygen source. This strategy has been applied to the synthesis of different important catechols with fluorescent property and bioactivity from the corresponding phenols. Finally, our method also provides a convenient route to 18O-labelled catechols using 18O-labelled acetic acid.

Suggested Citation

  • Qian Wu & Dingyuan Yan & Ying Chen & Ting Wang & Feng Xiong & Wei Wei & Yi Lu & Wei-Yin Sun & Jie Jack Li & Jing Zhao, 2017. "A redox-neutral catechol synthesis," Nature Communications, Nature, vol. 8(1), pages 1-9, April.
    • Handle: RePEc:nat:natcom:v:8:y:2017:i:1:d:10.1038_ncomms14227
    DOI: 10.1038/ncomms14227
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