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Nickel-catalysed retro-hydroamidocarbonylation of aliphatic amides to olefins

Author

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  • Jiefeng Hu

    (State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University)

  • Minyan Wang

    (State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University)

  • Xinghui Pu

    (State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University)

  • Zhuangzhi Shi

    (State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University)

Abstract

Amide and olefins are important synthetic intermediates with complementary reactivity which play a key role in the construction of natural products, pharmaceuticals and manmade materials. Converting the normally highly stable aliphatic amides into olefins directly is a challenging task. Here we show that a Ni/NHC-catalytic system has been established for decarbonylative elimination of aliphatic amides to generate various olefins via C–N and C–C bond cleavage. This study not only overcomes the acyl C–N bond activation in aliphatic amides, but also encompasses distinct chemical advances on a new type of elimination reaction called retro-hydroamidocarbonylation. This transformation shows good functional group compatibility and can serve as a powerful synthetic tool for late-stage olefination of amide groups in complex compounds.

Suggested Citation

  • Jiefeng Hu & Minyan Wang & Xinghui Pu & Zhuangzhi Shi, 2017. "Nickel-catalysed retro-hydroamidocarbonylation of aliphatic amides to olefins," Nature Communications, Nature, vol. 8(1), pages 1-7, August.
    • Handle: RePEc:nat:natcom:v:8:y:2017:i:1:d:10.1038_ncomms14993
    DOI: 10.1038/ncomms14993
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