This chapter presents a critical review of synthetically useful variations of ionic methods for hydrogenation of organic compounds. In practice ionic hydrogenation involves the formal introduction of hydride from a donor source to an electron‐deficient carbon center.
In this chapter, organosilicon hydrides are used as the source of ionic hydride with the goal of completing and updating earlier review work. Organosilicon compounds with at least one Si‐H bond have the ability to serve as mild‐air and water‐stable sources of hydrides and, thus, have reducing properties. In general, organosilicon hydrides do not undergo spontaneous reactions with organic compounds unless the organic substrate is a reasonably strong electrophile or the silane is first activated by the interaction of a nucleophilic species with a nucleophilic center. The organosilicon hydrides are covalent compounds that have little or no nucleophilic properties on their own. The use of these hydrides often provides a means of effecting reductions of organic substrates under very mild conditions and with excellent functional group selectivity. Consideration of the nature of the Si‐H bonds provides insight into the chemical behavior of these hydrides. Enhanced hydridic nature manifests itself in the chemical behavior of hydrosilanes.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.