Selective Alternate Derivatization of the Hexaphenylbenzene Framework through a Thermodynamically Controlled Halogen Dance
Selective Alternate Derivatization of the Hexaphenylbenzene Framework through a Thermodynamically Controlled Halogen Dance
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DOI：
10.1021/ol500041j
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发表时间：
2014-02-07
期刊：
影响因子：
5.2
通讯作者：
Hiraoka, Shuichi
中科院分区：
文献类型：
--
作者：
Kojima, Tatsuo;Hiraoka, Shuichi
我们报道了一个实用的合成方案和机理细节，通过热力学控制的卤素舞蹈选择性地交替衍生化六苯(HPB)骨架。HPB的交替三锂物种的稳定性可通过HPB骨架苯基的异构碳的穿透空间相互作用来解释。通过这种方法，在C-3对称和较低对称的HPB衍生物的外围具有两种或三种取代基变得容易和实用。
We report a practical synthetic protocol and mechanistic details for the selective alternate derivatization of the hexaphenylbenzene (HPB) framework through a thermodynamically controlled halogen dance. The stability of the alternately trilithiated species of HPB is interpreted by the through-space interaction at the ipso-carbons of the phenyl groups of the HPB framework. By using this approach, C-3-symmetric and lower-symmetric HPB derivatives possessing two or three kinds of substituents on the periphery have become easily and practically available.