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Synthesis of meta-carbonyl phenols and anilines

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  • Bao-Yin Zhao

    (Northwest University)

  • Qiong Jia

    (Northwest University)

  • Yong-Qiang Wang

    (Northwest University)

Abstract

Phenols and anilines are of extreme importance for medicinal chemistry and material science. The development of efficient approaches to prepare both compounds has thus long been a vital research topic. The utility of phenols and anilines directly reflects the identity and pattern of substituents on the benzenoid ring. Electrophilic substitutions remain among the most powerful synthetic methods to substituted phenols and anilines, yet in principle achieving ortho- and para-substituted products. Therefore, the selective preparation of meta-substituted phenols and anilines is the most significant challenge. We herein report an efficient copper-catalyzed dehydrogenation strategy to exclusively synthesize meta-carbonyl phenols and anilines from carbonyl substituted cyclohexanes. Mechanistic studies indicate that this transformation undergoes a copper-catalyzed dehydrogenation/allylic hydroxylation or amination/oxidative dehydrogenation/aromatization cascade process.

Suggested Citation

  • Bao-Yin Zhao & Qiong Jia & Yong-Qiang Wang, 2024. "Synthesis of meta-carbonyl phenols and anilines," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
  • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-46576-2
    DOI: 10.1038/s41467-024-46576-2
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    References listed on IDEAS

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    1. Franck Vaillant & Ana Mateos Calbet & Silvia González-Pelayo & Edward J. Reijerse & Shengyang Ni & Julia Busch & Josep Cornella, 2022. "Catalytic synthesis of phenols with nitrous oxide," Nature, Nature, vol. 604(7907), pages 677-683, April.
    2. Franck Vaillant & Ana Mateos Calbet & Silvia González-Pelayo & Edward J. Reijerse & Shengyang Ni & Julia Busch & Josep Cornella, 2022. "Author Correction: Catalytic synthesis of phenols with nitrous oxide," Nature, Nature, vol. 608(7922), pages 22-22, August.
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