Oxygen switch in visible-light photoredox catalysis: Radical additions and cyclizations and unexpected C-C-bond cleavage reactions

Shaoqun Zhu, Arindam Das, Lan Bui, Hanjun Zhou, Dennis P. Curran, Magnus Rueping*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

284 Scopus citations

Abstract

Visible light photoredox catalyzed inter- and intramolecular C-H functionalization reactions of tertiary amines have been developed. Oxygen was found to act as chemical switch to trigger two different reaction pathways and to obtain two different types of products from the same starting material. In the absence of oxygen, the intermolecular addition of N,N-dimethyl-anilines to electron-deficient alkenes provided γ-amino nitriles in good to high yields. In the presence of oxygen, a radical addition/cyclization reaction occurred which resulted in the formation of tetrahydroquinoline derivatives in good yields under mild reaction conditions. The intramolecular version of the radical addition led to the unexpected formation of indole-3-carboxaldehyde derivatives. Mechanistic investigations of this reaction cascade uncovered a new photoredox catalyzed C-C bond cleavage reaction.

Original languageEnglish (US)
Pages (from-to)1823-1829
Number of pages7
JournalJournal of the American Chemical Society
Volume135
Issue number5
DOIs
StatePublished - Feb 6 2013

ASJC Scopus subject areas

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

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