Synthesis of B/Si Bidentate Lewis Acids, o-(Fluorosilyl)(dimesitylboryl)benzenes, and Their Fluoride Ion Affinity

Atsushi Kawachi,* Atsushi Tani, Junpei Shimada, and Yohsuke Yamamoto
Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima 739-8526, Japan
J. Am. Chem. Soc., 2008, 130 (13), pp 4222–4223
DOI: 10.1021/ja710615r
Publication Date (Web): March 8, 2008
Copyright © 2008 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, kawachi@sci.hiroshima-u.ac.jp

Abstract

Abstract Image

o-(Fluorosilyl)(dimesitylboryl)benzenes have been prepared as colorless crystals by reacting fluorodimesitylborane with o-(fluorodimethylsilyl)phenyllithium and o-(fluorodiphenylsilyl)phenyllithium. The o-(fluorosilyl)(dimesitylboryl)benzenes serve as B/Si bidentate Lewis acid and efficiently capture fluoride ion from potassium fluoride in the presence of [2.2.2]cryptand or 18-crown-6 in toluene, giving the corresponding μ-fluoro bridged products. The structures were characterized by X-ray crystal structure analysis and multinuclear NMR spectroscopy. Fluoride ion affinities of the o-(fluorosilyl)(dimesitylboryl)benzenes were evaluated in comparison with non-silylated triarylborane.

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History

  • Published In Issue April 02, 2008
  • Received November 26, 2007

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