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B/Si双齿路易斯酸、-(氟硅基)硼苯和-(二氟硅基)硼苯的合成及其氟离子亲和性

Synthesis of B/Si Bidentate Lewis Acids, -(Fluorosilyl)borylbenzenes and -(Difluorosilyl)borylbenzenes, and Their Fluoride Ion Affinities.

作者信息

Shimada Junpei, Tani Atsushi, Hanazato Chihiro, Masuyama Takashi, Yamamoto Yohsuke, Kawachi Atsushi

机构信息

Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan.

Faculty of Bioscience and Applied Chemistry, Hosei University, 3-7-2 Kajino-cho, Koganei, Tokyo 184-8584, Japan.

出版信息

ACS Omega. 2022 Aug 23;7(35):30939-30953. doi: 10.1021/acsomega.2c02775. eCollection 2022 Sep 6.

DOI:10.1021/acsomega.2c02775
PMID:36092602
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9453949/
Abstract

Herein, we report detailed studies on a series of -(silyl)(boryl)benzenes (), in which the two Lewis acid centers consisting of silicon and boron atoms are linked via an -phenylene skeleton. -(Fluorosilyl)(dimesitylboryl)benzenes and were prepared by the reaction of fluorodimesitylborane with [-(fluorodimethylsilyl)phenyl]lithium () and [-(fluorodiphenylsilyl)phenyl]lithium (), respectively. -(Difluorosilyl)(dimesitylboryl)benzenes and were also prepared by the reaction of fluorodimesitylborane with -{[di(methoxy)methylsilyl]phenyl}lithium () and -{[di(methoxy)phenylsilyl]phenyl}lithium (), respectively, and their subsequent treatment with HF·pyridine. Compounds readily capture a fluoride ion in the presence of 18-crown-6 or [2.2.2]cryptand to afford their corresponding μ-fluoro-bridged ate complexes (). The structures of were revealed by NMR spectroscopy and X-ray crystallography. DFT studies and natural bond orbital analysis of were conducted to elucidate the nature of the Si-F and B-F bonding interactions in the μ-fluoro-bridges. The fluoride ion affinities of were investigated by H NMR spectroscopy to monitor their competitive reactions. The dynamic behaviors of at variable temperatures were monitored using F NMR spectroscopy.

摘要

在此，我们报告了一系列 -(硅基)(硼基)苯（）的详细研究，其中由硅和硼原子组成的两个路易斯酸中心通过 -亚苯基骨架相连。-(氟硅基)(二甲基硼基)苯 和 分别通过氟代二甲基硼烷与 [-(氟代二甲基硅基)苯基]锂（）和 [-(氟代二苯基硅基)苯基]锂（）反应制备。-(二氟硅基)(二甲基硼基)苯 和 也分别通过氟代二甲基硼烷与 -{[二(甲氧基)甲基硅基]苯基}锂（）和 -{[二(甲氧基)苯基硅基]苯基}锂（）反应，随后用 HF·吡啶处理制备。化合物 在 18-冠-6 或 [2.2.2]穴醚存在下容易捕获氟离子，得到其相应的 μ-氟桥连的酸根配合物（）。通过核磁共振光谱和 X 射线晶体学揭示了 的结构。对 进行了密度泛函理论研究和自然键轨道分析，以阐明 μ-氟桥中 Si-F 和 B-F 键相互作用的性质。通过 H 核磁共振光谱研究了 的氟离子亲和力，以监测它们的竞争反应。使用 F 核磁共振光谱监测了 在可变温度下的动态行为。

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