Catalytic olefin hydroamination with aminium radical cations: A photoredox method for direct C-N bond formation

Andrew J. Musacchio, Lucas Q. Nguyen, G. Hudson Beard, Robert R. Knowles

Research output: Contribution to journalArticle

136 Scopus citations

Abstract

While olefin amination with aminium radical cations is a classical method for C-N bond formation, catalytic variants that utilize simple 2° amine precursors remain largely undeveloped. Herein we report a new visible-light photoredox protocol for the intramolecular anti-Markovnikov hydroamination of aryl olefins that proceeds through catalytically generated aminium radical intermediates. Mechanistic studies are consistent with a process involving amine oxidation via electron transfer, turnover-limiting C-N bond formation, and a second electron transfer step to reduce a carbon-centered radical, rendering the overall process redox-neutral. A range of structurally diverse N-aryl heterocycles can be prepared in good to excellent yields under conditions significantly milder than those required by conventional aminium-based protocols.

Original languageEnglish (US)
Pages (from-to)12217-12220
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number35
DOIs
StatePublished - Sep 3 2014

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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