Synthesis of B/Si bidentate Lewis acids, o-(Fluorosilyl)(dimesitylboryl)benzenes, and their fluoride ion affinity.
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 mu-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.
Kawachi
Atsushi
A
Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima 739-8526, Japan. kawachi@sci.hiroshima-u.ac.jp
Tani
Atsushi
A
Shimada
Junpei
J
Yamamoto
Yohsuke
Y
D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D001667:Binding, Competitive; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D005459:Fluorides / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D017646:Organosilicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001555:Benzene Derivatives; D001896:Boron Compounds; D009942:Organometallic Compounds; D017646:Organosilicon Compounds; D008094:Lithium; D005459:Fluorides