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Copper-Catalyzed Intramolecular Dehydrogenative Aminooxygenation: Direct Access to Formyl-Substituted Aromatic N-Heterocycles

Authors

  • Honggen Wang,

    1. State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530 (China), Fax: (+86) 20-3201-5299
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  • Yong Wang,

    1. State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530 (China), Fax: (+86) 20-3201-5299
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  • Dongdong Liang,

    1. State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530 (China), Fax: (+86) 20-3201-5299
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  • Lanying Liu,

    1. State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530 (China), Fax: (+86) 20-3201-5299
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  • Prof. Dr. Jiancun Zhang,

    Corresponding author
    1. State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530 (China), Fax: (+86) 20-3201-5299
    • State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530 (China), Fax: (+86) 20-3201-5299
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  • Prof. Dr. Qiang Zhu

    Corresponding author
    1. State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530 (China), Fax: (+86) 20-3201-5299
    • State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou 510530 (China), Fax: (+86) 20-3201-5299
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  • We are grateful for financial support of this work by a Start-up Grant from Guangzhou Institutes of Biomedicine and Health (GIBH),and by the National Science Foundation of China (21072190) and the National Basic Research Program of China (973 Program 2011CB504004 and 2010CB945500). We thank Prof. Jinsong Liu (GIBH) for providing X-ray structural analysis.

Abstract

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A direct synthesis of carbaldehydes through intramolecular dehydrogenative aminooxygenation has been developed. The process uses a catalytic amount of copper(II) in DMF or DMA under oxygen and does not require additional oxidants (see scheme). Mechanistic studies suggest that the carbonyl oxygen atom of the aldehyde is derived from oxygen through a copper-mediated oxygen activation process via a peroxy–copper(III) intermediate.

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