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

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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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