Visible-light-induced, Ir-catalyzed reactions of N-methyl-N- ((trimethylsilyl)methyl)aniline with cyclic α,β-unsaturated carbonyl compounds

Dominik Lenhart, Thorsten Bach

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20 Scopus citations

Abstract

N-Methyl-N-((trimethylsilyl)methyl)aniline was employed as reagent in visible-light-induced, iridium-catalyzed addition reactions to cyclic α,β-unsaturated carbonyl compounds. Typical reaction conditions included the use of one equivalent of the reaction substrate, 1.5 equivalents of the aniline and 2.5 mol % (in MeOH) or 1.0 mol % (in CH2Cl2) [Ir(ppy)2(dtbbpy)]BF4 as the catalyst. Two major reaction products were obtained in combined yields of 3067%. One product resulted from aminomethyl radical addition, the other product was a tricyclic compound, which is likely formed by attack of the intermediately formed α-carbonyl radical at the phenyl ring. For five-membered α,β-unsaturated lactone and lactam substrates, the latter products were the only products isolated. For the six-membered lactones and lactams and for cyclopentenone the simple addition products prevailed.

Original languageEnglish
Pages (from-to)890-896
Number of pages7
JournalBeilstein Journal of Organic Chemistry
Volume10
DOIs
StatePublished - 17 Apr 2014

Keywords

  • Cyclization
  • Electron transfer
  • Iridium
  • Photochemistry
  • Photoredox catalysis
  • Radical reactions

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