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

Smith, Andrew J. and Dimitrova, Daniela and Arokianathar, Jude N. and Kolodziejczak, Krystian and Young, Allan and Allison, Mark and Poole, Darren L. and Leach, Stuart G. and Parkinson, John A. and Tuttle, Tell and Murphy, John A. (2020) New reductive rearrangement of N-Arylindoles triggered by the Grubbs-Stoltz reagent Et3SiH/KOtBu. Chemical Science, 11 (14). pp. 3719-3726. ISSN 2041-6539 (https://doi.org/10.1039/D0SC00361A)

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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

ORCID iDs

Smith, Andrew J. ORCID logoORCID: https://orcid.org/0000-0001-7848-076X, Dimitrova, Daniela, Arokianathar, Jude N. ORCID logoORCID: https://orcid.org/0000-0003-4770-2432, Kolodziejczak, Krystian, Young, Allan ORCID logoORCID: https://orcid.org/0000-0002-1525-4703, Allison, Mark ORCID logoORCID: https://orcid.org/0000-0001-5597-7175, Poole, Darren L., Leach, Stuart G., Parkinson, John A. ORCID logoORCID: https://orcid.org/0000-0003-4270-6135, Tuttle, Tell and Murphy, John A.;
  • Item type:Article
    ID code:71756
    Dates:
    Date
    Event
    14 April 2020
    Published
    11 March 2020
    Published Online
    11 March 2020
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:12 Mar 2020 13:56
    Last modified:21 Nov 2024 01:18
    URI:https://strathprints.strath.ac.uk/id/eprint/71756
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