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<p>Carboranes, unique three-dimensional analogs of benzene, have attracted considerable attention owing to their potential in medicine, catalysis, and materials science. Consequently, the introduction of functional groups into carborane clusters has emerged as an important research focus. While directing group-assisted <i>ortho</i>-B−H activation of <i>o</i>-carboranes is well established, <i>meta</i>-B−H functionalization remains rare. Here we show iridium(III)-catalyzed remote B(9)−H alkylation of <i>o</i>-carboranes using a nitrile-based directing template. Optimized template design is critical for achieving high efficiency and regioselectivity, as confirmed by experiments and density functional theory calculations. The method tolerates diverse functional groups, operates under simple conditions, and employs a removable template readily derived from <i>o</i>-carborane carboxylic acids. This approach enables scalable access to structurally diverse B(9)-alkylated <i>o</i>-carboranes for further synthetic elaboration.</p>

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Iridium(III)-catalyzed remote B(9)−H alkylation of o-carboranes with nitrile template

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年11月27日

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  • Kyungsup Lee,
  • Jiwon Kim,
  • Donghun Hwang,
  • Bora Yang,
  • Dayeon Kang,
  • Dongwook Kim,
  • Mu-Hyun Baik,
  • Phil Ho Lee

摘要

Carboranes, unique three-dimensional analogs of benzene, have attracted considerable attention owing to their potential in medicine, catalysis, and materials science. Consequently, the introduction of functional groups into carborane clusters has emerged as an important research focus. While directing group-assisted ortho-B−H activation of o-carboranes is well established, meta-B−H functionalization remains rare. Here we show iridium(III)-catalyzed remote B(9)−H alkylation of o-carboranes using a nitrile-based directing template. Optimized template design is critical for achieving high efficiency and regioselectivity, as confirmed by experiments and density functional theory calculations. The method tolerates diverse functional groups, operates under simple conditions, and employs a removable template readily derived from o-carborane carboxylic acids. This approach enables scalable access to structurally diverse B(9)-alkylated o-carboranes for further synthetic elaboration.