Mechanistic Guidance Leads to Enhanced Site-Selectivity in C–H Oxidation Reactions Catalyzed by Ruthenium bis(Bipyridine) Complexes,ACS Catalysis

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Mechanistic Guidance Leads to Enhanced Site-Selectivity in C–H Oxidation Reactions Catalyzed by Ruthenium bis(Bipyridine) Complexes
ACS Catalysis ( IF 11.3 ) Pub Date : 2021-08-09 , DOI: 10.1021/acscatal.1c02593
Jeremy D. Griffin ₁ , David B. Vogt ₁ , J. Du Bois ₂ , Matthew S. Sigman ₁

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The development of an operationally simple C–H oxidation protocol using an acid-stable, bis(bipyridine)Ru catalyst is described. Electronic differences remote to the site of C–H functionalization are found to affect product selectivity. Site-selectivity is further influenced by the choice of reaction solvent, with highest levels of 2° methylene oxidation favored in aqueous dichloroacetic acid. A statistical model is detailed that correlates product selectivity outcomes with computational parameters describing the relative “electron-richness” of C–H bonds.

中文翻译：

机理指导提高了钌双（联吡啶）配合物催化的 C-H 氧化反应的位点选择性

描述了使用酸稳定的双（联吡啶）Ru 催化剂开发操作简单的 C-H 氧化方案。发现远离 C-H 功能化位点的电子差异会影响产品的选择性。位点选择性进一步受反应溶剂选择的影响，在二氯乙酸水溶液中，2° 亚甲基氧化的水平最高。详细的统计模型将产品选择性结果与描述 C-H 键的相对“电子丰富度”的计算参数相关联。

更新日期：2021-08-20

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