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Copper-Catalyzed Aerobic Intramolecular Dehydrogenative Cyclization of N,N-Disubstituted Hydrazones through Cmath image[BOND]H Functionalization

Authors

  • Dr. Guangwu Zhang,

    1. Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)
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  • Yan Zhao,

    1. Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)
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  • Prof. Dr. Haibo Ge

    Corresponding author
    1. Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)
    • Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, IN 46202 (USA)
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  • We gratefully acknowledge Indiana University Purdue University Indianapolis for financial support. The Bruker 500 MHz NMR was purchased using funds from an NSF-MRI award (CHE-0619254). We also would like to thank Jinmin Miao for providing several starting materials.

Abstract

original image

Eine aerobe Aktivierung: Die Titelreaktion verläuft über eine Sequenz aus Oxidation, Cyclisierung und Aromatisierung unter einer O2-Atmosphäre (siehe Schema; DBU=1,8-Diazabicyclo[5.4.0]undec-7-en, DCE=1,2-Dichlorethan, DMS=Dimethylsulfid). Diese Kupplung ist die erste Cmath image-H-Bindungsfunktionalisierung, die über ein Iminium-Intermediat verläuft, und bietet einen schonenden und atomeffizienten Zugang zu substituierten Pyrazolen.

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