Visible Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination- and Iminohydroxylation-Cyclization Reactions

Research output: Contribution to journalArticle

  • Authors:
  • Jacob Davies
  • Samuel G. Booth
  • Stephanie Essafi
  • Robert A W Dryfe
  • Daniele Leonori

Abstract

The formation and use of iminyl radicals in novel and divergent hydroimination and iminohydroxylation cyclization reactions has been accomplished through the design of a new class of reactive O-aryl oximes. Owing to their low reduction potentials, the inexpensive organic dye eosin Y could be used as the photocatalyst of the organocatalytic hydroimination reaction. Furthermore, reaction conditions for a unique iminohydroxylation were identified; visible-light-mediated electron transfer from novel electron donor–acceptor complexes of the oximes and Et3N was proposed as a key step of this process.

Bibliographical metadata

Original languageEnglish
Pages (from-to)14017-14021
Number of pages4
JournalAngewandte Chemie (International Edition)
Volume54
Issue number47
DOIs
StatePublished - 28 Sep 2015