Mechanistic Aspects of Hydrosilane/Potassium tert-Butoxide (HSiR3/KOtBu)-Mediated Reactions
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Accepted Manuscript (AM)
Author(s)
Jenkins, Ian D
Krenske, Elizabeth H
Griffith University Author(s)
Year published
2020
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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/KOtBu-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 ...
View more >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/KOtBu-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/KOtBu reagent system. Several mechanistic phenomena that remain to be explained are also highlighted.
View less >
View more >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/KOtBu-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/KOtBu reagent system. Several mechanistic phenomena that remain to be explained are also highlighted.
View less >
Journal Title
ACS Omega
Volume
5
Issue
13
Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Omega, © 2020 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acsomega.0c00366
Subject
Chemical sciences
Chemical engineering
Materials engineering