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<p>The cyano group is a versatile motif in medicinal chemistry, serving as both a target and a precursor to other functional groups. However, direct deaminative cyanation of aliphatic amines remains a challenge due to the inertness of C–N bonds and the instability of amines under oxidative conditions. Here we report a catalytic, direct deaminative cyanation of aliphatic primary amines without preactivation. This method employs an anomeric amide for radical generation from amines and TMSCN as the cyano source, with a copper catalyst and N-fluorosulfonamide reagent cooperatively facilitating both radical coupling and propagation. This work integrates anomeric amide activation with transition-metal-catalysed bond formation. The strategy enables not only efficient cyanation but also asymmetric deaminative cyanation, stereocentre inversion and downstream transformations such as homologation and CO insertion, providing versatile tools for amine diversification.</p><p></p>

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Direct copper-catalysed deaminative cyanation of aliphatic primary amines

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年7月10日

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  • Jiang-Hao Xue,
  • Shuang Lin,
  • Jiawu Huang,
  • Taeseok Kang,
  • Bumsu Park,
  • Mark D. Levin,
  • Myojeong Kim,
  • Honggen Wang

摘要

The cyano group is a versatile motif in medicinal chemistry, serving as both a target and a precursor to other functional groups. However, direct deaminative cyanation of aliphatic amines remains a challenge due to the inertness of C–N bonds and the instability of amines under oxidative conditions. Here we report a catalytic, direct deaminative cyanation of aliphatic primary amines without preactivation. This method employs an anomeric amide for radical generation from amines and TMSCN as the cyano source, with a copper catalyst and N-fluorosulfonamide reagent cooperatively facilitating both radical coupling and propagation. This work integrates anomeric amide activation with transition-metal-catalysed bond formation. The strategy enables not only efficient cyanation but also asymmetric deaminative cyanation, stereocentre inversion and downstream transformations such as homologation and CO insertion, providing versatile tools for amine diversification.