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首页> 外文期刊>Chemistry: A European journal >Kumada–Corriu Cross-Couplings with 2-Pyridyl Grignard Reagents
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Kumada–Corriu Cross-Couplings with 2-Pyridyl Grignard Reagents

机译：具有2-吡啶基格氏试剂的Kumada–Corriu交叉偶联

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Substituted heterobiaryls constitute privileged scaffolds of compounds with activities of relevance to various research areas, ranging from medicinal chemistry and catalysis to material sciences.[1–4] Their regioselective syntheses rely strongly on transition-metal-catalyzed cross-coupling reactions, which have matured to being indispensable tools in modern organic syntheses.[3, 4] Since organomagnesium reagents are more readily available than are alternative organometallic nucleophiles,[5, 6] catalytic cross-couplings of Grignard reagents have proven particularly useful for streamlining heterobiaryl synthesis.[7] Therefore, catalysts derived from various transition metals, such as nickel,[8, 9] palladium,[10] iron,[11, 12] cobalt,[13–15] or manganese,[16] were developed for Kumada–Corriu-type[17, 18] coupling reactions.[3, 4, 19] While this research significantly expanded the pool of viable electrophiles, cross-coupling reactions of electron-deficient N-heterocyclic nucleophiles continue to be challenging because of their reduced nucleophilicities. Hence, a generally applicable protocol for metal-catalyzed arylations of less nucleophilic 2-azine Grignard[20] reagents has, to the best of our knowledge, proven elusive.[2, 21, 22] As part of our program directed towards the use of air-stable secondary phosphine oxides (SPO) as preligands in transition-metal atalysis,[23, 24] we noted that efficient cross-couplings with 2-pyridyl organomagnesium compounds could be accomplished, provided that palladium catalysts derived from air- and moisturestable SPOs[23] were employed as preligands. Herein, we report on these findings, which highlight the unique reactivity profile of SPO preligands.
机译：取代的杂二芳基化合物构成特权化合物，其活性与药物化学和催化到材料科学等各个研究领域相关。[1-4]它们的区域选择性合成强烈依赖于过渡金属催化的交叉偶联反应，该反应已经成熟。 [3，4]由于有机镁试剂比其他有机金属亲核试剂更容易获得，[5，6]格氏试剂的催化交叉偶联已被证明对简化杂二芳基合成特别有用。[7 ]因此，针对Kumada-Corriu-类型[17，18]偶联反应。[3，4，19]尽管这项研究显着扩大了可行的亲电试剂池，但缺电子的N杂环亲核试剂的交叉偶联反应由于其亲核性降低而继续具有挑战性。因此，据我们所知，一种普遍适用的较少亲核性2-嗪格氏试剂[20]的金属催化的芳基化方案难以证明。[2，21，22]稳定的二次氧化膦（SPO）作为过渡金属催化中的配体，[23，24]我们注意到，只要衍生自空气和水分稳定的钯催化剂，就可以实现与2-吡啶基有机镁化合物的有效交叉偶联SPO [23]被用作优先配体。本文中，我们对这些发现进行了报道，这些发现突出了SPO配体的独特反应性。

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