Pd-Catalyzed Aerobic Oxidative Coupling of Thiophenes: Synergistic Benefits of Phenanthroline Dione and a Cu Cocatalyst,Journal of the American Chemical Society

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Pd-Catalyzed Aerobic Oxidative Coupling of Thiophenes: Synergistic Benefits of Phenanthroline Dione and a Cu Cocatalyst
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-11-06 , DOI: 10.1021/jacs.0c09962
Stephen J Tereniak ₁ , David L Bruns ₁ , Shannon S Stahl ₁

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Substituted bithiophenes are prominent fragments in functional organic materials, and they are ideally prepared via direct oxidative C-H/C-H coupling. Here, we report a novel PdII catalyst system, employing 1,10-phenanthroline-5,6-dione (phd) as the ancillary ligand, that enables aerobic oxidative homocoupling of 2-bromothiophenes and other related heterocycles. These observations represent the first use of phd to support Pd-catalyzed aerobic oxidation. The reaction also benefits from a Cu(OAc)2 cocatalyst, and mechanistic studies show that Cu promotes C-C coupling, implicating a role for CuII different from its conventional contribution to reoxidation of the Pd catalyst.

中文翻译：

钯催化的噻吩有氧氧化偶联：菲咯啉二酮和铜助催化剂的协同效益

取代联噻吩是功能有机材料中的重要片段，它们理想地通过直接氧化CH/CH偶联制备。在这里，我们报道了一种新型 PdII 催化剂系统，采用 1,10-菲咯啉-5,6-二酮 (phd) 作为辅助配体，能够实现 2-溴噻吩和其他相关杂环的有氧氧化自偶联。这些观察结果代表了首次使用 phd 来支持 Pd 催化的有氧氧化。该反应还受益于 Cu(OAc)2 助催化剂，机理研究表明 Cu 促进 CC 偶联，这表明 CuII 对 Pd 催化剂再氧化的作用不同于其传统贡献。

更新日期：2020-11-06

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