Transition-Metal-Mediated Three-Component Cascade Cyclization: Selective Cage B–C(sp2) Coupling of Carborane with Aromatics and Synthesis of Carborane-Fused Tricyclics,Journal of the American Chemical Society

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Transition-Metal-Mediated Three-Component Cascade Cyclization: Selective Cage B–C(sp2) Coupling of Carborane with Aromatics and Synthesis of Carborane-Fused Tricyclics
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2014-05-16 , DOI: 10.1021/ja503489b
Yangjian Quan ₁ , Zaozao Qiu ₂ , Zuowei Xie _{1,

2}

Affiliation

Zirconium/nickel comediated one-pot three-component cascade cyclization of carboryne, alkene, and 2-bromophenyltrimethylsilylacetylene has been achieved, leading to the formation of a series of C,C,B-substituted carborane-fused tricyclics. On the basis of experimental results, a plausible mechanism is proposed including [2 + 2 + 1] cross-cyclotrimerization followed by intramolecular direct selective cage B-C(sp(2)) coupling. This represents the first example of direct cage B-C(phenyl) coupling via cage B-H activation.

中文翻译：

过渡金属介导的三组分级联环化：碳硼烷与芳烃的选择性笼式 B-C(sp2) 偶联和碳硼烷稠合三环化合物的合成

已经实现了锆/镍共介导的碳炔、烯烃和 2-溴苯基三甲基甲硅烷基乙炔的一锅三组分级联环化，形成了一系列 C、C、B 取代的碳硼烷稠合三环化合物。根据实验结果，提出了一种合理的机制，包括 [2 + 2 + 1] 交叉环三聚，然后是分子内直接选择性笼 BC(sp(2)) 耦合。这代表了通过笼 BH 活化直接笼 BC(苯基) 偶联的第一个例子。

更新日期：2014-05-16

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