Anomalous Reactivity of Silylborane: Transition-Metal-Free Boryl Substitution of Aryl, Alkenyl, and Alkyl Halides with Silylborane/Alkoxy Base Systems

作者:Yamamoto Eiji; Izumi Kiyotaka; Horita Yuko; Ito Hajime*
来源:Journal of the American Chemical Society, 2012, 134(49): 19997-20000.
DOI:10.1021/ja309578k

摘要

An unexpected borylation of organic halides with a silyborane in the presence of an alkoxy base has been observed. This formal nucleophilic boryl substitution can be applied to a broad range of substrates with high functional group compatibility. Even sterically hindered aryl bromides afforded the corresponding boryl compounds in high yields. Preliminary mechanistic studies indicated that this boryl substitution is promoted by neither transition-metal contamination nor a radical-mediated process.

  • 出版日期2012-12-12