Palladium-Catalyzed Regiospecific peri- and ortho-C–H Oxygenations of Polyaromatic Rings Mediated by Tunable Directing Groups,Organic Letters

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Palladium-Catalyzed Regiospecific peri- and ortho-C–H Oxygenations of Polyaromatic Rings Mediated by Tunable Directing Groups
Organic Letters ( IF 4.9 ) Pub Date : 2020-12-22 , DOI: 10.1021/acs.orglett.0c03701
Jing Jiang ₁ , Dandan Yuan ₁ , Congzhe Ma ₁ , Wanbin Song ₁ , Yaoyu Lin ₁ , Lihong Hu ₁ , Yinan Zhang ₁

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An efficient divergent approach of Pd-catalyzed C–H oxygenation of polyaromatic rings is described. Reversible directing groups enable regiospecific peri- and ortho-oxygenation to readily access a wide array of polyaromatic phenols without pre- and postmanipulation of directing groups. The systematic mechanistic investigation, including deuterium-labeling experiments, palladacycle trapping, and DFT calculations, reveals that the tunable ligand-assisted C–H bond cleavage played a crucial role during the reaction process.

中文翻译：

钯催化区域专一围和邻- C-H由可调聚芳环介导的氧合定位基团

描述了Pd催化的多环芳烃环氧化的高效发散方法。可逆导向组使区域专一围和邻氧合容易地访问一个宽的聚芳族酚的阵列而不前和定位基团的postmanipulation。系统的机理研究，包括氘标记实验，保拉达环捕集和DFT计算，揭示了可调节的配体辅助的C–H键裂解在反应过程中起着至关重要的作用。

更新日期：2021-01-16

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