Transition Metal Free Cycloamination of Prenyl Carbamates and Ureas Promoted by Aryldiazonium Salts

Roman Abrams, Quentin Lefebvre, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

12 Citations (Scopus)
149 Downloads (Pure)

Abstract

Upon treatment with aryldiazonium salts, prenyl carbamates and ureas undergo redox-neutral azocycloamination. In general, N-aryl O-prenyl carbamates cyclize in a photocatalytic reaction with visible light and an organic dye. With electron-deficient diazonium salts, electronic matching with an electron-rich N-aryl substituent results in a reaction proceeding in the ground state, without either light or photocatalyst. Cyclic voltammetry suggests that this radical reaction is initiated by hydrogen-atom abstraction mediated by an aryl radical, followed by a radical addition cascade and proton-coupled hole propagation. The reaction proceeds at room temperature in short reaction times, and a range of functional groups is tolerated.

Original languageEnglish
Pages (from-to)13587-13591
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number41
Early online date17 Sep 2018
DOIs
Publication statusPublished - 8 Oct 2018

Keywords

  • amination
  • cyclizations
  • diazonium salts
  • heterocycles
  • radicals

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