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<p>Chlorine-substituted ketones are crucial intermediates in organic synthesis, and acyl chlorination of chemical feedstocks employing commercially available benzoyl chloride provides an atom-and-step economic route for their synthesis. While atom-transfer radical addition (ATRA) has proven effective for 1,2-acyl chlorination, the efficient realization of 1,3-acyl chlorination has remained a considerable challenge. In this study, an NHC/photocatalyst dual-catalyzed system was developed to facilitate the 1,3-acyl chlorination of cyclopropanes using benzoyl chloride as a bifunctional reagent. This strategy also enables the synthesis of acyl-cyclopropanes with quaternary carbon centers through a nucleophilic annulation process. The practical utility of this approach was demonstrated through large-scale synthesis, product derivatization, and the preparation of analogs of anti-psychotics, including haloperidol, melperone and fluanisone.</p>

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Visible light-mediated 1,3-acylative chlorination of cyclopropanes employing benzoyl chloride as bifunctional reagents in NHC catalysis

  • 期刊论文

  • 发表日期：

    2025年3月10日

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  • Mingrui Li,
  • Xiao Song,
  • Xueyun Lu,
  • Jiuli Xia,
  • Guangfan Zheng,
  • Qian Zhang

摘要

Chlorine-substituted ketones are crucial intermediates in organic synthesis, and acyl chlorination of chemical feedstocks employing commercially available benzoyl chloride provides an atom-and-step economic route for their synthesis. While atom-transfer radical addition (ATRA) has proven effective for 1,2-acyl chlorination, the efficient realization of 1,3-acyl chlorination has remained a considerable challenge. In this study, an NHC/photocatalyst dual-catalyzed system was developed to facilitate the 1,3-acyl chlorination of cyclopropanes using benzoyl chloride as a bifunctional reagent. This strategy also enables the synthesis of acyl-cyclopropanes with quaternary carbon centers through a nucleophilic annulation process. The practical utility of this approach was demonstrated through large-scale synthesis, product derivatization, and the preparation of analogs of anti-psychotics, including haloperidol, melperone and fluanisone.