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<p>Trifluoromethyl carbyne (CF<sub>3</sub>Ċ:), with its three non-bonded electrons, has the potential to form three new chemical bonds. Herein, we explore a novel photocatalytic trifunctionalization of trifluoromethyl carbyne to synthesize 1-(het)aryl-2,2,2-trifluoroethyl 2-iodobenzoate, which is further converted into <i>α</i>-(het)aryl trifluoromethylcarbinols of interest in medicinal chemistry through a hydrolysis process. To improve the practicality of this reaction and streamline the procedure, we achieve the assembly of <i>α</i>-(het)aryl trifluoromethylcarbinols in a one-step reaction under mild conditions by adding LiPF and H<sub>2</sub>O. A plausible catalytic pathway involves the direct C(<i>sp</i><sup>2</sup>)-H bond diazotrifluoromethylation of (het)arenes with the diazotrifluoroethyl radical (N<sub>2</sub>=Ċ-CF<sub>3</sub>) generated from hypervalent iodine(III) reagent, followed by N<sub>2</sub> extrusion and subsequent O-H bond insertion with H<sub>2</sub>O to form <i>α</i>-(het)aryl(trifluoromethyl) carbenes. This efficient tandem process enables the one-pot, step-economical synthesis of <i>α</i>-aryl 2,2,2-trifluoroethanol derivatives, representing a unique approach for the straightforward synthesis of trifluoromethylcarbinols.</p>

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Trifluoromethylcarbinolation of (hetero)arenes enabled by trifluoromethyl carbyne

  • 期刊论文

  • 发表日期：

    2025年7月2日

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  • Meng-Yang Tian,
  • Yong-Chao Shao,
  • Wen-Wen Zhao,
  • Zhi-Yu Lang,
  • Jian-Fei Zhao,
  • Yong-Jian Lu,
  • Chun-Yang He,
  • Yong-Zheng Chen,
  • Wen-Yong Han

摘要

Trifluoromethyl carbyne (CF3Ċ:), with its three non-bonded electrons, has the potential to form three new chemical bonds. Herein, we explore a novel photocatalytic trifunctionalization of trifluoromethyl carbyne to synthesize 1-(het)aryl-2,2,2-trifluoroethyl 2-iodobenzoate, which is further converted into α-(het)aryl trifluoromethylcarbinols of interest in medicinal chemistry through a hydrolysis process. To improve the practicality of this reaction and streamline the procedure, we achieve the assembly of α-(het)aryl trifluoromethylcarbinols in a one-step reaction under mild conditions by adding LiPF and H2O. A plausible catalytic pathway involves the direct C(sp2)-H bond diazotrifluoromethylation of (het)arenes with the diazotrifluoroethyl radical (N2=Ċ-CF3) generated from hypervalent iodine(III) reagent, followed by N2 extrusion and subsequent O-H bond insertion with H2O to form α-(het)aryl(trifluoromethyl) carbenes. This efficient tandem process enables the one-pot, step-economical synthesis of α-aryl 2,2,2-trifluoroethanol derivatives, representing a unique approach for the straightforward synthesis of trifluoromethylcarbinols.