Boryl substitution of functionalized aryl-, heteroaryl- and alkenyl halides with silylborane and an alkoxy base: expanded scope and mechanistic studies

Eiji Yamamoto, Satoshi Ukigai, Hajime Ito

研究成果: ジャーナルへの寄稿学術誌査読

56 被引用数 (Scopus)

抄録

A transition-metal-free method has been developed for the boryl substitution of functionalized aryl-, heteroaryl- and alkenyl halides with a silylborane in the presence of an alkali-metal alkoxide. The base-mediated boryl substitution of organohalides with a silylborane was recently reported to provide the corresponding borylated products in good to high yields, and exhibit good functional group compatibility and high tolerance to steric hindrance. In this study, the scope of this transformation has been extended significantly to include a wide variety of functionalized aryl-, heteroaryl- and alkenyl halides. In particular, the boryl substitution of (E)- and (Z)-alkenyl halides proceeded smoothly to afford the corresponding alkenyl boronates in good to high yields with retention of the configuration using modified reaction conditions. The results of the mechanistic studies suggest that this boryl substitution proceeds via a carbanion-mediated mechanism.

本文言語英語
ページ(範囲)2943-2951
ページ数9
ジャーナルChemical Science
6
5
DOI
出版ステータス出版済み - 5月 1 2015
外部発表はい

!!!All Science Journal Classification (ASJC) codes

  • 化学 (全般)

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