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<p>Anionic ligands capable of forming covalent bonds with metal centers serve as a powerful tool for precisely modulating the stereoelectronic properties of catalysts. However, the development and application of chiral anionic ligands in transition metal-catalyzed asymmetric synthesis remain underexplored. Here, we report a chiral anionic ProPhenol ligand, which effectively facilitates the nickel-catalyzed asymmetric synthesis of chiral (hetero)aryl and alkenyl sulfinamides under mild reaction conditions. Remarkably, this catalytic system exhibits exceptional efficiency, achieving high yields and stereoselectivity control with only 0.5 mol% catalyst loading in 5 mmol-scale reactions, underscoring its practical synthetic utility. Comprehensive density functional theory (DFT) calculations reveal that the oxygen-boron interaction between the ligand and substrate plays a critical role in facilitating the transmetalation process, while hydrogen-bonding interactions between the ligand and trityl sulfinylamine (TrNSO) significantly enhance enantioselectivity in this transformation.</p>

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Chiral anionic ProPhenol ligand enabled nickel catalyzed enantioselective synthesis of sulfinamides

  • 期刊论文

  • 发表日期：

    2025年8月25日

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  • Ya-Qian Zhang,
  • Yuxiang Zhang,
  • Jiazhong Tang,
  • Jiajun Wu,
  • Jingjing Xue,
  • Zijian Chen,
  • Qing-Wei Zhang

摘要

Anionic ligands capable of forming covalent bonds with metal centers serve as a powerful tool for precisely modulating the stereoelectronic properties of catalysts. However, the development and application of chiral anionic ligands in transition metal-catalyzed asymmetric synthesis remain underexplored. Here, we report a chiral anionic ProPhenol ligand, which effectively facilitates the nickel-catalyzed asymmetric synthesis of chiral (hetero)aryl and alkenyl sulfinamides under mild reaction conditions. Remarkably, this catalytic system exhibits exceptional efficiency, achieving high yields and stereoselectivity control with only 0.5 mol% catalyst loading in 5 mmol-scale reactions, underscoring its practical synthetic utility. Comprehensive density functional theory (DFT) calculations reveal that the oxygen-boron interaction between the ligand and substrate plays a critical role in facilitating the transmetalation process, while hydrogen-bonding interactions between the ligand and trityl sulfinylamine (TrNSO) significantly enhance enantioselectivity in this transformation.