Synthesis of Rationally Halogenated Buckybowls by Chemoselective Aromatic C-F Bond Activation
Synthesis of Rationally Halogenated Buckybowls by Chemoselective Aromatic C-F Bond Activation
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DOI：
10.1002/anie.201700814
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发表时间：
2017-04-18
影响因子：
16.6
通讯作者：
Amsharov, Konstantin Y.
中科院分区：
文献类型：
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作者：
Papaianina, Olena;Akhmetov, Vladimir A.;Amsharov, Konstantin Y.
卤代巴基碗或碗状多环芳烃（BS-PAH）是“自下而上”合成各种碳基纳米材料的关键构件，在不同的技术领域具有突出的潜力。目前的技术水平提供了相当有限的合成途径BS-PAH的数量，而且，这些方法都没有表现出高的选择性和耐受性的官能团。在这里，我们证明了一个有效的路线BS多环芳烃，包括直接分子内芳基-芳基耦合通过C-F键活化。的耦合条件被发现是完全容忍对芳香族C-Br和C-Cl键，从而允许轻松合成的合理卤代巴基碗具有前所未有的选择性水平。这一发现为无法通过替代方法获得的功能化BS-PAH系统开辟了道路。
Halogenated buckybowls or bowl-shaped polycyclic aromatic hydrocarbons (BS-PAHs) are key building blocks for the "bottom-up" synthesis of various carbon-based nanomaterials with outstanding potential in different fields of technology. The current state of the art provides quite a limited number of synthetic pathways to BS-PAHs; moreover, none of these approaches show high selectivity and tolerance of functional groups. Herein we demonstrate an effective route to BS-PAHs that includes directed intramolecular aryl-aryl coupling through C-F bond activation. The coupling conditions were found to be completely tolerant toward aromatic C-Br and C-Cl bonds, thus allowing the facile synthesis of rationally halogenated buckybowls with an unprecedented level of selectivity. This finding opens the way to functionalized BS-PAH systems that cannot be obtained by alternative methods.