Mechanistic Aspects of Hydrosilane/Potassium tert-Butoxide (HSiR3/KO t Bu)-Mediated Reactions

Ian D Jenkins; Elizabeth H Krenske

doi:10.1021/acsomega.0c00366

Mechanistic Aspects of Hydrosilane/Potassium tert-Butoxide (HSiR₃/KO ^t Bu)-Mediated Reactions

ACS Omega. 2020 Mar 23;5(13):7053-7058. doi: 10.1021/acsomega.0c00366. eCollection 2020 Apr 7.

Authors

Ian D Jenkins¹, Elizabeth H Krenske²

Affiliations

¹ Griffith Institute for Drug Discovery, Griffith University, Nathan, QLD 4111, Australia.
² School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, QLD 4072, Australia.

Abstract

The hydrosilane/potassium tert-butoxide reagent system has attracted significant attention over the last 5 years since the discovery of its ability to silylate heteroarene C-H bonds. Numerous useful HSiR₃/KO ^t Bu-mediated transformations are now known, including silylation of sp, sp², and sp³ C-H bonds, reductive cleavage of C-O, C-S, and C-N bonds, reduction of polycyclic arenes, and hydrosilylation and polymerization of styrenes. This mini-review surveys the rich diversity of reaction mechanisms, both ionic and free radical and including hydride transfer, H atom transfer, and electron transfer, that have been uncovered during recent studies on the HSiR₃/KO ^t Bu reagent system. Several mechanistic phenomena that remain to be explained are also highlighted.

Publication types

Review