Et3SiH + KOtBu provide multiple reactive intermediates that compete in the reactions and rearrangements of benzylnitriles and indolenines

Smith, Andrew J. and Dimitrova, Daniela and Arokianathar, Jude N. and Clark, Kenneth F. and Poole, Darren L. and Leach, Stuart G. and Murphy, John A. (2020) Et3SiH + KOtBu provide multiple reactive intermediates that compete in the reactions and rearrangements of benzylnitriles and indolenines. Chemical Science, 11 (45). pp. 12364-12370. ISSN 2041-6520 (https://doi.org/10.1039/D0SC04244G)

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Abstract

The combination of potassium tert-butoxide and triethylsilane is unusual because it generates multiple different types of reactive intermediates simultaneously that provide access to (i) silyl radical reactions, (ii) hydrogen atom transfer reactions to closed shell molecules and to radicals, (iii) electron transfer reductions and (iv) hydride ion chemistry, giving scope for unprecedented outcomes. Until now, reactions with this reagent pair have generally been explained by reference to one of the intermediates, but we now highlight the interplay and competition between them.

  • Item type:Article
    ID code:74440
    Dates:
    Date
    Event
    7 December 2020
    Published
    21 October 2020
    Published Online
    21 October 2020
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:29 Oct 2020 15:15
    Last modified:09 Apr 2024 01:56
    URI:https://strathprints.strath.ac.uk/id/eprint/74440
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