Deprotonation of diphenylsilane with organosilyllithium agents

Abstract

Although there are many reports on deprotonation of carbon analogues, there are only a few reports on deprotonation from silanes. This is because the lone pair of a base mainly attacks hydrogen of a C–H bond and deprotonates, whereas in the case of silanes, the base is added to the silicon atom of a Si–H bond. Previous reports have shown that deprotonation from silanes requires the assistance of negative hyperconjugation by silyl substituents or intramolecular chelating groups (pincer ligands). We proposed that lithium and hydrogen exchange approach could be applied to the deprotonation of monosilanes using bulky silyllithium instead of some bulky strong bases, such as t-butyllithium and LDA. Here, we report the first successful approach to the deprotonation of monosilanes without intramolecular chelation.