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Issue 11, 2019
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Nickel-catalyzed oxidative C–H/N–H annulation of N-heteroaromatic compounds with alkynes

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Abstract

The reaction of N-heteroaromatic compounds, such as 2-aryl-pyrrole, benzimidazole, imidazole, indole, and pyrazole derivatives, with alkynes in the presence of a catalytic amount of a nickel complex results in C–H/N–H oxidative annulation. The reaction shows a high functional group compatibility. While both Ni(0) and Ni(II) complexes show a high catalytic activity, Ni(0) is proposed as a key catalytic species in the main catalytic cycle. In the case of the Ni(II) system, the presence of a catalytic amount of a strong base, such as KOBut, is required for the reaction to proceed. In sharp contrast, a base is not required in the case of the Ni(0) system. The proposed mechanism is supported by DFT studies.

Graphical abstract: Nickel-catalyzed oxidative C–H/N–H annulation of N-heteroaromatic compounds with alkynes

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Publication details

The article was received on 14 Nov 2018, accepted on 03 Feb 2019 and first published on 04 Feb 2019


Article type: Edge Article
DOI: 10.1039/C8SC05063E
Citation: Chem. Sci., 2019,10, 3242-3248
  • Open access: Creative Commons BY-NC license
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    Nickel-catalyzed oxidative C–H/N–H annulation of N-heteroaromatic compounds with alkynes

    A. Obata, A. Sasagawa, K. Yamazaki, Y. Ano and N. Chatani, Chem. Sci., 2019, 10, 3242
    DOI: 10.1039/C8SC05063E

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