Facile preparation of organosilanes from benzylboronates and -diborylalkanes mediated by KOBu

• Published in: Chemical science (Cambridge) 2023-07, Vol.14 (26), p.7355-736
• Main Authors: Tang, Man, Zhu, Wenyan, Sun, Huaxing, Wang, Jing, Jing, Su, Wang, Minyan, Shi, Zhuangzhi, Hu, Jiefeng
• Format: Article
• ISSN: 2041-6520; 2041-6539
• DOI: 10.1039/d3sc02461j

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. A deboronative silylation of readily available benzylboronates and diborylalkanes with chlorosilanes has been developed using an alkoxide base. This approach enables the synthesis of benzyl silanes and silylboronates in practical and selective ways.