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首页> 外文期刊>Chemistry: A European journal >Rhodium/Phosphine/Amine·HBr Catalyst System for Highly Selective Cross-Cyclodimerization of Aryl- and AlkylACHTUNGTRENUNGalkynes: Efficient Access to Multisubstituted Naphthalene Derivatives
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Rhodium/Phosphine/Amine·HBr Catalyst System for Highly Selective Cross-Cyclodimerization of Aryl- and AlkylACHTUNGTRENUNGalkynes: Efficient Access to Multisubstituted Naphthalene Derivatives

机译：铑/膦/胺/ HBr催化体系，用于芳基和烷基的高度选择性交叉环二聚反应：ACHTUNGTRENUNG炔烃：有效获得多取代萘衍生物

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Various polysubstituted aromatic compounds have long been of great significance in the chemical and pharmaceutical industries. In particular, those with polycyclic p-conjugated structures have recently become increasingly important in the area of organic electronics.[1] The transition-metalmediated annulative benzene ring homologation with alkynes or their equivalents[2–6] is one of the modern potential synthetic strategies to prepare naphthalenes and higher fused aromatics. As one of the early examples, Sakakibara[2a] and Heck[2b] independently reported the palladium-catalyzed annulation reaction of aryl halide with two acetylenedicarboxylate or diphenylacetylene molecules to construct the naphthalene skeletons. Takahashi described the homologation reaction with o-dihalobenzenes and zirconacyclopentadienes.[3] Our groups also focused on this methodology and succeeded in the formation of polysubstituted naphthalenes and anthracenes from internal alkynes and benzoyl chlorides or benzoic acids accompanied by decarbonylation or decarboxylation.[4] In addition, the recent advances of benzyne chemistry provide an efficient route to fused aromatics involving anthracenes and phenanthrenes by using o-dibromobenzene or o-trimethylsilylphenyl triflates as the starting materials.[5] However, the processes mentioned above require the leaving groups on the benzene rings so that the inevitable wastes, such as the metal salts, are produced simultaneously. Recently, we reported the rhodium-catalyzed oxidative homologation of directing-group-containing arenes with alkynes through two sp2 C-H bond cleavages.[7] Wu also has described the palladium-catalyzed similar type of transformation with electron-rich arenes, such as p-xylene, under oxidative conditions.[8] While these procedures are useful because preactivation of the arene moieties could be eliminated, a stoichiometric amount of oxidant, CuACHTUNGTRENUNG(OAc)2 or AgOAc, is required. From the viewpoint of atom economy, further development of different protocols for the synthesis of the multisubstituted aromatics from relatively simple hydrocarbons is strongly desired.
机译：长期以来，各种多取代的芳族化合物在化学和制药工业中一直具有重要意义。特别是，具有多环p共轭结构的化合物最近在有机电子领域变得越来越重要。[1]过渡金属介导的苯环与炔烃或其等同物的同系物[2-6]是制备萘和高级稠合芳烃的现代潜在合成策略之一。作为较早的例子之一，Sakakibara [2a]和Heck [2b]独立地报道了钯催化的芳基卤化物与两个乙炔二羧酸盐或二苯乙炔分子的环化反应，以构建萘骨架。高桥描述了与邻二卤代苯和氧化锆环戊二烯的同源反应。[3]我们的小组也关注这种方法，并成功地从内部炔烃和苯甲酰氯或苯甲酸伴随脱羰基或脱羧基形成了多取代的萘​​和蒽。[4]另外，最新的苯甲醛化学进展为邻苯二溴苯或邻三甲基甲硅烷基苯基三氟甲磺酸酯为原料提供了一种有效的途径来合成包括蒽和菲的稠合芳烃。[5]但是，上述方法需要在苯环上具有离去基团，从而不可避免地产生了废料，例如金属盐。最近，我们报道了铑通过两个sp2 C-H键断裂与炔烃一起催化含导基团的芳烃的氧化同源性。[7] Wu还描述了在氧化条件下，钯催化类似类型的富电子芳烃（如对二甲苯）的转化。[8]尽管这些程序很有用，因为可以消除芳烃部分的预活化，但需要化学计量的氧化剂CuACHTUNGTRENUNG（OAc）2或AgOAc。从原子经济的观点出发，强烈期望进一步开发用于从相对简单的烃合成多取代的芳族化合物的不同方案。

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