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

Research output: Contribution to journalArticle

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.
Original languageEnglish
Number of pages7
JournalChemical Science
Early online date21 Oct 2020
DOIs
Publication statusE-pub ahead of print - 21 Oct 2020

Keywords

  • benzylnitriles
  • indolenines
  • hydrogen aton transfer

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