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<p><i>N</i>-CF<sub>3</sub> amides are promising targets for pharmaceutical and agrochemistry. Unfortunately, there is a defluorination problem of <i>N</i>-CF<sub>3</sub> amine starting materials when using common amide bond formation method. Recently, elegant alternative approaches emerged. However, none have used the well known amidyl radical chemistry to directly prepare <i>N</i>-CF<sub>3</sub> amides. We describe here a convenient preparation of <i>N</i>-(<i>N</i>-CF<sub>3</sub> imidoyloxy) pyridinium salts and their applications as efficient trifluoromethylamidyl radical precursors in photocatalytic trifluoromethylamidations of (hetero)arenes, alkenes, alkynes, silylenol ethers, and isocyanides. The rapid construction of diverse <i>N</i>-CF<sub>3</sub> amides, particularly the synthesis of cyclic <i>N</i>-CF<sub>3</sub> amides, demonstrates the uniqueness and flexibility of the method. This method is expected to provide a platform for directly synthesizing <i>N</i>-CF<sub>3</sub> amides and to inspire the discovery of more redox molecular systems that can handle challenging trifluoromethylamidations.</p>

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Direct synthesis of N-trifluoromethyl amides via photocatalytic trifluoromethylamidation

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年5月28日

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  • Ru Zhong Zhang,
  • Yang Liu,
  • Cong Xu,
  • Mang Wang

摘要

N-CF3 amides are promising targets for pharmaceutical and agrochemistry. Unfortunately, there is a defluorination problem of N-CF3 amine starting materials when using common amide bond formation method. Recently, elegant alternative approaches emerged. However, none have used the well known amidyl radical chemistry to directly prepare N-CF3 amides. We describe here a convenient preparation of N-(N-CF3 imidoyloxy) pyridinium salts and their applications as efficient trifluoromethylamidyl radical precursors in photocatalytic trifluoromethylamidations of (hetero)arenes, alkenes, alkynes, silylenol ethers, and isocyanides. The rapid construction of diverse N-CF3 amides, particularly the synthesis of cyclic N-CF3 amides, demonstrates the uniqueness and flexibility of the method. This method is expected to provide a platform for directly synthesizing N-CF3 amides and to inspire the discovery of more redox molecular systems that can handle challenging trifluoromethylamidations.