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May 15, 2026ChemistrySelect0 citations

Metal‐Free α‐Amino‐C(sp 3 )‐H Imidation of N ‐Benzyl Amides

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JBJean Le Bras

Key Points

  • This research aims to explore a metal-free method for the imidation of C(sp3)-H sites in N-benzyl amides.
  • Utilized N-bromoimides as the imide source for the reaction
  • Involved N-bromination of the amide, followed by deprotonation and nucleophilic addition of the imide
  • Produced a variety of amido aminal structures with high selectivity
  • Successfully demonstrated selective formation of amido aminal groups without transition metals
  • Detailed the three-step reaction mechanism involved
  • Collected preliminary data indicating reaction feasibility and efficiency

Abstract

ABSTRACT Herein, we report the imidation of the C(sp 3 )─H adjacent to the nitrogen atom of N ‐benzyl amides, leading to a variety of amido aminal structures, using N ‐bromoimides as the imide source. The reaction does not employ transition metals and is highly selective towards the formation of the amido aminal group. Preliminary studies indicated that the reaction would occur through three consecutive steps: N ‐bromination of the amide, deprotonation, and nucleophilic addition of in situ‐formed imide.

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Cite This Study

Jean Le Bras (2026) studied this question.

synapsesocial.com/papers/6a06b95be7dec685947ac01bhttps://doi.org/10.1002/slct.73478
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