Cooperative Light-Activated Iodine and Photoredox Catalysis for the Amination of Csp3 −H Bonds

Peter Becker, Thomas Duhamel, Christopher J. Stein, Markus Reiher, Kilian Muñiz

Research output: Contribution to journalArticlepeer-review

166 Scopus citations

Abstract

An unprecedented method that makes use of the cooperative interplay between molecular iodine and photoredox catalysis has been developed for dual light-activated intramolecular benzylic C−H amination. Iodine serves as the catalyst for the formation of a new C−N bond by activating a remote C sp3 −H bond (1,5-HAT process) under visible-light irradiation while the organic photoredox catalyst TPT effects the reoxidation of the molecular iodine catalyst. To explain the compatibility of the two involved photochemical steps, the key N−I bond activation was elucidated by computational methods. The new cooperative catalysis has important implications for the combination of non-metallic main-group catalysis with photocatalysis.

Original languageEnglish
Pages (from-to)8004-8008
Number of pages5
JournalAngewandte Chemie International Edition in English
Volume56
Issue number27
DOIs
StatePublished - 26 Jun 2017
Externally publishedYes

Keywords

  • 1,5-HAT processes
  • amination
  • cooperative catalysis
  • iodine catalysis
  • photoredox catalysis

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