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Bisphosphines: A Prominent Ancillary Ligand Class for Application in Nickel-Catalyzed C–N Cross-Coupling
ACS Catalysis ( IF 11.3 ) Pub Date : 2018-06-20 00:00:00 , DOI: 10.1021/acscatal.8b01879 Christopher M. Lavoie 1 , Mark Stradiotto 1
ACS Catalysis ( IF 11.3 ) Pub Date : 2018-06-20 00:00:00 , DOI: 10.1021/acscatal.8b01879 Christopher M. Lavoie 1 , Mark Stradiotto 1
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The Ni-catalyzed Csp2–N cross-coupling of NH substrates and (hetero)aryl (pseudo)halides for the synthesis of (hetero)anilines is in the midst of a resurgence. Reactivity breakthroughs that have been achieved in this field within the past five years have served to establish Ni catalysis as being competitive with, and in some cases superior to, more well-established Pd- or Cu-based protocols. Whereas the repurposing of useful ancillary ligands from the Pd domain has been the most frequently employed approach in the quest to develop effective Ni-based catalysts for such transformations, considerable progress has been made as of late in the design of ancillary ligands tailored specifically for use with Ni. Bisphosphine ancillary ligands have proven to be well-suited for such an approach, given their modular and facile syntheses; several variants have emerged recently that are particularly effective in enabling a range of otherwise challenging Ni-catalyzed Csp2–N cross-couplings. This Perspective presents a comprehensive summary of the advancements within the field of Ni-catalyzed Csp2–N cross-coupling through the application of the bisphosphine ancillary ligand class. It is our intention that the discussion of key ancillary ligand design concepts and mechanistic considerations presented herein will provide a useful platform for researchers to initiate ancillary ligand design efforts for the development of high-performing Ni cross-coupling catalysts.
中文翻译：
双膦：在镍催化的C–N交叉偶联中应用的突出的辅助配体类别
Ni催化的C sp2NH底物和（杂）芳基（假）卤化物的-N交叉偶联正在用于（杂）苯胺的合成。在过去的五年中，该领域取得的反应性突破已使Ni催化与成熟的基于Pd或Cu的方法相比具有竞争优势，并且在某些情况下优于某些基于Pd或Cu的方法。从Pd结构域重新利用有用的辅助配体是寻求开发用于此类转化的有效Ni基催化剂的最常用方法，但直到最近，专门为使用而设计的辅助配体的设计都取得了相当大的进步。和倪 鉴于双膦辅助配体的模块化和便捷合成，事实证明它们非常适合这种方法。sp2 –N交叉耦合。该观点通过应用双膦类辅助配体类别全面概述了镍催化的C sp2 -N交叉偶联领域的研究进展。我们的意图是，本文介绍的关键辅助配体设计概念和机理考虑因素的讨论将为研究人员启动辅助配体设计工作以开发高性能Ni交叉偶联催化剂提供有用的平台。
更新日期：2018-06-20
中文翻译：
双膦：在镍催化的C–N交叉偶联中应用的突出的辅助配体类别
Ni催化的C sp2NH底物和（杂）芳基（假）卤化物的-N交叉偶联正在用于（杂）苯胺的合成。在过去的五年中，该领域取得的反应性突破已使Ni催化与成熟的基于Pd或Cu的方法相比具有竞争优势，并且在某些情况下优于某些基于Pd或Cu的方法。从Pd结构域重新利用有用的辅助配体是寻求开发用于此类转化的有效Ni基催化剂的最常用方法，但直到最近，专门为使用而设计的辅助配体的设计都取得了相当大的进步。和倪 鉴于双膦辅助配体的模块化和便捷合成，事实证明它们非常适合这种方法。sp2 –N交叉耦合。该观点通过应用双膦类辅助配体类别全面概述了镍催化的C sp2 -N交叉偶联领域的研究进展。我们的意图是，本文介绍的关键辅助配体设计概念和机理考虑因素的讨论将为研究人员启动辅助配体设计工作以开发高性能Ni交叉偶联催化剂提供有用的平台。
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