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Highly chemoselective synthesis of hindered amides via cobalt-catalyzed intermolecular oxidative hydroamidation

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  • Yun-Nian Yin

    (Peking University)

  • Rui-Qi Ding

    (Peking University)

  • Dong-Chen Ouyang

    (Peking University)

  • Qing Zhang

    (Peking University)

  • Rong Zhu

    (Peking University)

Abstract

α-Tertiary amides are of great importance for medicinal chemistry. However, they are often challenging to access through conventional methods due to reactivity and chemoselectivity issues. Here, we report a single-step approach towards such amides via cobalt-catalyzed intermolecular oxidative hydroamidation of unactivated alkenes, using nitriles of either solvent- or reagent-quantities. This protocol is selective for terminal alkenes over groups that rapidly react under known carbocation amidation conditions such as tertiary alcohols, electron-rich alkenes, ketals, weak C−H bonds, and carboxylic acids. Straightforward access to a diverse array of hindered amides is demonstrated, including a rapid synthesis of an aminoadamantane-derived pharmaceutical intermediate.

Suggested Citation

  • Yun-Nian Yin & Rui-Qi Ding & Dong-Chen Ouyang & Qing Zhang & Rong Zhu, 2021. "Highly chemoselective synthesis of hindered amides via cobalt-catalyzed intermolecular oxidative hydroamidation," Nature Communications, Nature, vol. 12(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-22373-z
    DOI: 10.1038/s41467-021-22373-z
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