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Next-generation functional surfactant for mild C−H arylation under micellar conditions
Chem Catalysis ( IF 11.5 ) Pub Date : 2024-10-10 , DOI: 10.1016/j.checat.2024.101146
Pascal Hauk, Sven Trienes, Fabrice Gallou, Lutz Ackermann, Joanna Wencel-Delord

Micellar reaction conditions have emerged as a powerful and sustainable strategy in synthetic organic chemistry. Numerous transformations have been reported to work under micellar conditions; however, transformations such as C−H activation remain scarce, and the compartmentalization effects are not yet fully understood. Herein, we describe a rational surfactant design for challenging C−H activation. Incorporating a pyridone ligand into a commercially available PS-750-M surfactant allows for overcoming the compartmentalization issues, resulting in an efficient Ru-catalyzed direct arylation under mild reaction conditions and with excellent selectivity. Physicochemical characterization of this surfactant shed light on the inherent properties of the novel PyOH-750-M surfactant while recycling of the surfactant allows for product formation with a low E-factor of 5.5 without a drop in reactivity.

中文翻译:


用于胶束条件下温和 C-H 芳基化的下一代功能性表面活性剂



胶束反应条件已成为合成有机化学中一种强大且可持续的策略。据报道,许多转化在胶束条件下起作用;然而,诸如 C-H 激活之类的转化仍然很少,并且区室化效应尚未完全了解。在本文中,我们描述了一种用于挑战 C-H 活化的合理表面活性剂设计。将吡啶酮配体掺入市售的 PS-750-M 表面活性剂中可以克服区室化问题,从而在温和的反应条件下实现高效的 Ru 催化直接芳基化反应,并具有出色的选择性。这种表面活性剂的物理化学表征揭示了新型 PyOH-750-M 表面活性剂的固有特性,而表面活性剂的回收允许形成具有 5.5 低 E 因子的产品,而不会降低反应性。
更新日期:2024-10-10
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