Facile preparation of organosilanes from benzylboronates and gem-diborylalkanes mediated by KOtBu

Methods to efficiently synthesize organosilanes are valuable in the fields of synthetic chemistry and materials science. During the past decades, boron conversion has become a generic and powerful approach for constructing carbon-carbon and other carbon-heteroatom bonds, but its potential application in forming carbon-silicon remains unexplored. Herein, we describe an alkoxide base-promoted deborylative silylation of benzylic organoboronates, geminal bis(boronates) or alkyltriboronates, allowing for straightforward access to synthetically valuable organosilanes. This selective deborylative methodology exhibits operational simplicity, broad substrate scope, excellent functional group compatibility and convenient scalability, providing an effective and complementary platform for the generation of diversified benzyl silanes and silylboronates. Detailed experimental results and calculated studies revealed an unusual mechanistic feature of this C-Si bond formation.

Automated summary

Efficient synthesis methods for organosilanes are important in the fields of synthetic chemistry and materials science. In this study, an alkoxide base-promoted deborylative silylation reaction was developed, providing straightforward access to valuable organosilanes. This method demonstrates operational simplicity, broad substrate scope, excellent functional group compatibility, and convenient scalability, making it an effective and complementary platform for generating diversified benzyl silanes and silylboronates. Detailed experimental results and mechanistic studies revealed unique features of the C-Si bond formation.