Non-Symmetrical Bis-Azine Biaryls from Chloroazines: A Strategy Using Phosphorus Ligand-Coupling,Journal of the American Chemical Society

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Non-Symmetrical Bis-Azine Biaryls from Chloroazines: A Strategy Using Phosphorus Ligand-Coupling
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2019-09-04 , DOI: 10.1021/jacs.9b08504
Benjamin T Boyle ₁ , Michael C Hilton ₁ , Andrew McNally ₁

Affiliation

Distinct approaches to synthesize bis-azine biaryls are in demand as these compounds have multiple applications in the chemical sciences and are challenging targets for metal-catalyzed cross-coupling reactions. Most approaches focus on developing new reagents as the formal nucleophilic coupling partner that can function in metal-catalyzed processes. We present an alternative approach using pyridine and diazine phosphines as nucleophilic partners and chloroazines where the heterobiaryl bond is formed via a tandem SNAr-phosphorus ligand-coupling sequence. The heteroaryl phosphines are prepared from chloroazines and are bench-stable solids. A range of bis-azine biaryls can be formed from abundant chloroazines using this strategy that would be challenging using traditional approaches. A one-pot cross-electrophile coupling of two chloroazines is feasible, and we also compared the phosphorus-mediated strategy with metal-catalyzed coupling reactions to show advantages and compatibility.

中文翻译：

来自氯嗪的非对称双氮杂二芳基化合物：一种使用磷配体偶联的策略

需要独特的方法来合成双嗪联芳基化合物，因为这些化合物在化学科学中有多种应用，并且是金属催化交叉偶联反应的挑战性目标。大多数方法侧重于开发新试剂，作为可以在金属催化过程中发挥作用的正式亲核偶联伙伴。我们提出了一种替代方法，使用吡啶和二嗪膦作为亲核伙伴和氯嗪，其中杂联芳键是通过串联 SNAr-磷配体偶联序列形成的。杂芳基膦由氯嗪制备并且是长期稳定的固体。使用这种策略可以从丰富的氯嗪中形成一系列双嗪联芳基化合物，这对于使用传统方法来说是具有挑战性的。

更新日期：2019-09-04

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