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Palladium-catalyzed carbonylative Sonogashira cross-coupling for the synthesis of alkynones with formic acid as the CO source

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Abstract

A practical and efficient palladium-catalyzed carbonylative Sonogashira cross-coupling reaction for the synthesis of alkynones from aryl iodides, alkynes, and formic acid as the CO source has been described. Under the assistance of PPh3/I2, formic acid can be used as the CO source for synthesis of alkynones in moderate–good yields. Furthermore, it is also successfully applied for the modification of natural products, such as vindoline and tabersonin, to obtain the corresponding products.

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Acknowledgements

This work was supported by Special Fund for Strategic Pilot Technology Chinese Academy of Sciences (XDA12040303).

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Authors and Affiliations

  1. Shanghai Research Center for Modernization of Traditional Chinese Medicine, National Engineering Laboratory for TCM Standardization Technology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, People’s Republic of China

    Xue Lyu, Guanglong Sun, Yang Zhou, Yingying Wang, Min Lei, Wanying Wu & Dean Guo

  2. University of Chinese Academy of Sciences, Beijing, 100049, People’s Republic of China

    Xue Lyu, Guanglong Sun, Yang Zhou, Yingying Wang, Min Lei, Wanying Wu & Dean Guo

Authors
  1. Xue Lyu
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  2. Guanglong Sun
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  3. Yang Zhou
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  4. Yingying Wang
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  5. Min Lei
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  6. Wanying Wu
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  7. Dean Guo
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Correspondence to Min Lei or Wanying Wu.

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Lyu, X., Sun, G., Zhou, Y. et al. Palladium-catalyzed carbonylative Sonogashira cross-coupling for the synthesis of alkynones with formic acid as the CO source. Monatsh Chem 150, 309–315 (2019). https://doi.org/10.1007/s00706-018-2331-7

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  • DOI: https://doi.org/10.1007/s00706-018-2331-7

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