Adaptive Photochemical Amination via Co(II) Catalysis,Journal of the American Chemical Society

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Adaptive Photochemical Amination via Co(II) Catalysis
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2024-09-18 , DOI: 10.1021/jacs.4c08130
Geyang Song ₁ , Jiameng Song ₁ , Qi Li ₁ , Tengfei Kang ₁ , Jianyang Dong ₁ , Gang Li ₁ , Juan Fan ₁ , Chao Wang ₁ , Dong Xue ₁

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Transition-metal-catalyzed amination of aryl halides is one of the most employed methods for constructing N-arylation adducts. However, the broad success of these reactions largely relies on the screening of precatalysts, elaborated ligands, and case-by-case optimization of reaction conditions (solvent, base, additive, temperature, etc.) for electronically or structurally diverse nucleophiles. Herein, we report an adaptive photochemical C–N coupling of aryl halides with various nitrogen nucleophiles (aliphatic and aromatic amines, amides, sulfonamides, pyrazoles, and ammonium salts) by Co(II) catalysis under the same reaction conditions (same precatalyst, same ligand, same base, same solvent, same temperature) without the addition of any exogenous photocatalyst. This photochemical amination features a wide substrate scope (>130 examples, up to 95% yield) with excellent functional group tolerance. Mechanistic studies indicate that these C–N coupling reactions may proceed via a Co(I)/Co(III) catalytic cycle.

中文翻译：

通过 Co（II）催化进行适应性光化学胺化

芳基卤化物的过渡金属催化胺化是构建 N-芳基化加合物最常用的方法之一。然而，这些反应的广泛成功在很大程度上取决于预催化剂的筛选、详细的配体以及针对电子或结构多样化的亲核试剂的反应条件（溶剂、碱、添加剂、温度等）的逐案优化。在此，我们报道了芳基卤化物与各种亲氮核试剂（脂肪族和芳香族胺、酰胺、磺胺、吡唑和铵盐）在相同反应条件（相同预催化剂、相同配体、相同碱、相同溶剂、相同温度）下通过 Co（II）催化的适应性光化学 C-N 偶联，无需添加任何外源性光催化剂。这种光化学胺化反应具有广泛的底物范围（>130 实例，高达 95% 的产率）和优异的官能团耐受性。机理研究表明，这些 C-N 偶联反应可以通过 Co（I）/Co（III）催化循环进行。

更新日期：2024-09-18

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