Synthesis of biaryl compounds through three-component assembly:: Ambidentate effect of the tert-butyldimethylsilyl group for regioselective Diels-Alder and Hiyama coupling reactions
Synthesis of biaryl compounds through three-component assembly:: Ambidentate effect of the tert-butyldimethylsilyl group for regioselective Diels-Alder and Hiyama coupling reactions
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DOI：
10.1002/anie.200803011
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发表时间：
2008-01-01
影响因子：
16.6
通讯作者：
Kita, Yasuyuki
中科院分区：
文献类型：
--
作者：
Akai, Shuji;Ikawa, Takashi;Kita, Yasuyuki
联芳基部分普遍存在于天然产物、[1a-c]药物、[1d，e]聚合物、[1f]传感器[1g]和过渡金属催化剂的配体中。[1h已经开发了许多用于制备这些化合物的有用方法，这些方法基于芳基卤化物与芳基金属物质通过Stille、Suzuki、Negishi和Hiyama反应的过渡金属催化的交叉偶联。[2]多组分组装方案已被认为是制备分子复杂性和多样性的有力手段，因此特别适用于组合化学和多样性导向的合成。[3]作为实现该目标的方法，我们现在报道了通过组装以下三种组分来制备多取代的不对称联芳基化合物的新方法：甲硅烷基化的苯炔、呋喃衍生物和芳基碘[Eq.①]。因此，该方法包括通过3-叔丁基二甲基甲硅烷基苯炔的区域选择性Diels-Alder反应构建甲硅烷基萘衍生物
The biaryl moiety is ubiquitous in natural products,[1a–c] pharmaceuticals,[1d, e] polymers,[1f] sensors,[1g] and in ligands for transition-metal catalysts.[1h, i] A number of useful methods for the preparation of these compounds have been developed based on the transition-metal-catalyzed cross-coupling of aryl halides with aryl metal species through Stille, Suzuki, Negishi, and Hiyama reactions.[2]Multicomponent assembly protocols have been recognized as a powerful means for the preparation of molecular complexity and diversity, and are thus particularly suited for combinatorial chemistry and diversity-oriented synthesis.[3] As an approach towards this goal, we now report the novel preparation of multisubstituted unsymmetrical biaryl compounds through the assembly of the following three components: a silylated benzyne, a furan derivative, and an aryl iodide [Eq.(1)]. Thus, this methodology involves the construction of silylnaphthalene derivatives by a regioselective Diels–Alder reaction of 3-tert-butyldimethylsilylbenzynes