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<p>The streamlined dual-functional group transfer (streamlined dual-FGT) strategy represents an efficient and sustainable approach for difunctionalization reactions, where all atoms or functional groups from the starting materials are fully incorporated into the final products without generating by-products. Pyridine and nitrile functionalities are prevalent and highly valued structural motifs found in a myriad of natural products, pharmaceuticals, agrochemicals, and polymers. The simultaneous incorporation of these groups via the streamlined dual-FGT strategy is thus of considerable significance in synthetic chemistry. Herein, we report a regioselective pyridylcyanation of internal alkynes enabled by an oxalate-based photocatalytic system, employing cyanopyridine as a streamlined dual-functional group transfer reagent. Mechanistic investigations using time-resolved spectroscopy reveal that the transformation proceeds through a photoinduced regioselective radical addition of the persistent cyanopyridine radical anion to alkynes, followed by the cooperative release and re-addition of the cyanide ion (CN⁻).</p>

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Photocatalytic streamlined dual-functional group transfer from cyanopyridine to internal alkynes

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年10月9日

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  • Xiaogang Tong,
  • Jialong Jie,
  • Yan Liu,
  • Haihan Yu,
  • Mingquan Yuan,
  • Hwee Ting Ang,
  • Gan Wang,
  • Duanshuai Tian,
  • Hongmei Su,
  • Jie Wu

摘要

The streamlined dual-functional group transfer (streamlined dual-FGT) strategy represents an efficient and sustainable approach for difunctionalization reactions, where all atoms or functional groups from the starting materials are fully incorporated into the final products without generating by-products. Pyridine and nitrile functionalities are prevalent and highly valued structural motifs found in a myriad of natural products, pharmaceuticals, agrochemicals, and polymers. The simultaneous incorporation of these groups via the streamlined dual-FGT strategy is thus of considerable significance in synthetic chemistry. Herein, we report a regioselective pyridylcyanation of internal alkynes enabled by an oxalate-based photocatalytic system, employing cyanopyridine as a streamlined dual-functional group transfer reagent. Mechanistic investigations using time-resolved spectroscopy reveal that the transformation proceeds through a photoinduced regioselective radical addition of the persistent cyanopyridine radical anion to alkynes, followed by the cooperative release and re-addition of the cyanide ion (CN⁻).