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<p>The dehydrogenative aromatisation of cyclohexanone derivatives has had a transformative influence on the synthesis of aromatic compounds because functional groups can be easily introduced at desired positions via classic organic reactions without being limited by <i>ortho</i>-, <i>meta</i>- or <i>para</i>-orientations. However, research is still limited on acceptorless dehydrogenative aromatisation, especially with regard to nonprecious-metal catalysts. Ni is a promising candidate catalyst as a congener of Pd, but thermally Ni-catalysed dehydrogenative aromatisation has not been reported even in an oxidative manner because of the difficulty of β-hydride elimination and the fast re-insertion of Ni–H species. Here, we report a CeO<sub>2</sub>-supported Ni(0) nanoparticle catalyst for acceptorless dehydrogenative aromatisation of cyclohexanone derivatives. This catalyst is widely applicable to various compounds such as cyclohexanols, cyclohexylamines, <i>N</i>-heterocycles, enamines and β-heteroatom-substituted ketones. Through various experiments, we demonstrate that the present reaction was achieved by the concerted catalysis utilizing metal ensembles unique to supported metal nanoparticle catalysts.</p>

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Ni-catalysed acceptorless dehydrogenative aromatisation of cyclohexanones enabled by concerted catalysis specific to supported nanoparticles

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年2月7日

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  • Takehiro Matsuyama,
  • Takafumi Yatabe,
  • Tomohiro Yabe,
  • Kazuya Yamaguchi

摘要

The dehydrogenative aromatisation of cyclohexanone derivatives has had a transformative influence on the synthesis of aromatic compounds because functional groups can be easily introduced at desired positions via classic organic reactions without being limited by ortho-, meta- or para-orientations. However, research is still limited on acceptorless dehydrogenative aromatisation, especially with regard to nonprecious-metal catalysts. Ni is a promising candidate catalyst as a congener of Pd, but thermally Ni-catalysed dehydrogenative aromatisation has not been reported even in an oxidative manner because of the difficulty of β-hydride elimination and the fast re-insertion of Ni–H species. Here, we report a CeO2-supported Ni(0) nanoparticle catalyst for acceptorless dehydrogenative aromatisation of cyclohexanone derivatives. This catalyst is widely applicable to various compounds such as cyclohexanols, cyclohexylamines, N-heterocycles, enamines and β-heteroatom-substituted ketones. Through various experiments, we demonstrate that the present reaction was achieved by the concerted catalysis utilizing metal ensembles unique to supported metal nanoparticle catalysts.