N-tosylhydrazones as acceptors for nucleophilic alkyl radicals in photoredox catalysis: A short case study on possible side reactions

Anna G. Kinsella, Joshua D. Tibbetts, Darren Stead, Alexander J. Cresswell

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Abstract

We report the attempted development of a photoredox-catalyzed α-C–H alkylation reaction of aliphatic amine derivatives, using N-tosylhydrazones as radical alkylating partners. The original intention was to intercept α-aminoalkyl radical intermediates with N-tosylhydrazones, followed by the expulsion of a sulfonyl radical by β-scission to generate N-H diazene species. Facile denitrogenation of these intermediates would remove all traces of the hydrazone moiety and provide a net C–H alkylation process. However, our plans were derailed by issues with the low reactivity of N-tosylhydrazones toward intermolecular capture by nucleophilic radicals, and several unexpected side reactions. Our findings, though unsuccessful, do serve to identify challenges for future researchers attempting to develop similar transformations.

Original languageEnglish
Pages (from-to)413-423
Number of pages11
JournalSynthetic Communications
Volume52
Issue number3
Early online date21 Jan 2022
DOIs
Publication statusPublished - 31 Dec 2022

Keywords

  • Amines
  • hydrazones
  • photoredox
  • radicals
  • side reactions

ASJC Scopus subject areas

  • Organic Chemistry

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