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Palladium-catalyzed oxidative cyclopropanation of enamides and norbornenes initiated by C–H activation

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Abstract

A novel palladium-catalyzed oxidative cyclopropanation of enamides and norbornenes has been developed. The reaction proceeded through palladium-catalyzed vinyl C–H bond activation of enamides followed by two migratory insertions, β-(N)H elimination and hydrolyzation cascade steps. The reaction tolerates a range of functional groups and provides an effective method for the synthesis of cyclopropane-fused norbornanes in good yields under mild conditions.

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Acknowledgments

This work was supported by the National Natural Science Foundation of China (NSFC-21622203, 21472147, 21702161), the China Postdoctoral Science Foundation Funded Project (2017M610644), and Fund of Northwest University (334100036).

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Authors and Affiliations

  1. Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi’an, 710127, China

    Ming Chen, Mi-Na Zhao, Yao-Du Zhang, Zhi-Hui Ren & Zheng-Hui Guan

  2. Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, 721013, China

    Mi-Na Zhao

Authors
  1. Ming Chen
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  2. Mi-Na Zhao
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  3. Yao-Du Zhang
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  4. Zhi-Hui Ren
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  5. Zheng-Hui Guan
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Correspondence to Zheng-Hui Guan.

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Chen, M., Zhao, MN., Zhang, YD. et al. Palladium-catalyzed oxidative cyclopropanation of enamides and norbornenes initiated by C–H activation. Sci. China Chem. 61, 695–701 (2018). https://doi.org/10.1007/s11426-017-9150-x

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  • DOI: https://doi.org/10.1007/s11426-017-9150-x

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