New reductive rearrangement of N-Arylindoles triggered by the Grubbs-Stoltz reagent Et3SiH/KOtBu

Andrew J. Smith, Daniela Dimitrova, Jude N. Arokianathar, Krystian Kolodziejczak, Allan Young, Mark Allison, Darren L. Poole, Stuart G. Leach, John A. Parkinson, Tell Tuttle, John A. Murphy

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)
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Abstract

N-Arylindoles are transformed into dihydroacridines in a new type of rearrangement, through heating with triethylsilane and potassium tert-butoxide. Studies indicate that the pathway involves (i) the formation of indole radical anions followed by fragmentation of the indole C2-N bond, and (ii) a ring-closing reaction that follows a potassium-ion dependent hydrogen atom transfer step. Unexpected behaviors of ‘radical-trap’ substrates prove very helpful in framing the proposed mechanism
Original languageEnglish
Pages (from-to)3719-3726
Number of pages8
JournalChemical Science
Volume11
Issue number14
Early online date11 Mar 2020
DOIs
Publication statusPublished - 14 Apr 2020

Keywords

  • N-Arylindoles
  • Grubbs-Stoltz reagent
  • dihydroacridines

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