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

Andrew J. Smith, Daniela Dimitrova, Jude N. Arokianathar, Kenneth F. Clark, Darren L. Poole, Stuart G. Leach, John A. Murphy

Research output: Contribution to journalArticlepeer-review

3 Downloads (Pure)

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
Pages (from-to)12364-12370
Number of pages7
JournalChemical Science
Volume11
Issue number45
Early online date21 Oct 2020
DOIs
Publication statusPublished - 7 Dec 2020

Keywords

  • benzylnitriles
  • indolenines
  • hydrogen aton transfer

Fingerprint Dive into the research topics of 'Et<sub>3</sub>SiH + KOtBu provide multiple reactive intermediates that compete in the reactions and rearrangements of benzylnitriles and indolenines'. Together they form a unique fingerprint.

Cite this