Tunable Rh(III)-Catalyzed C(sp2)–H Bond Functionalization of Aryl Imidates with Cyclic 1,3-Diones: Strategic Use of Directing Groups,Organic Letters

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Tunable Rh(III)-Catalyzed C(sp2)–H Bond Functionalization of Aryl Imidates with Cyclic 1,3-Diones: Strategic Use of Directing Groups
Organic Letters ( IF 4.9 ) Pub Date : 2024-09-06 , DOI: 10.1021/acs.orglett.4c02819
Junnan E ₁ , Luohe Wang ₁ , Jing Zeng ₁ , Hua Tian ₂ , Xiubin Bu ₁ , Xiaobo Yang _{1,

3} , Zhen Zhao ₁

Affiliation

A tunable Rh(III)-catalyzed C(sp²)–H bond functionalization of aryl imidates with cyclic 1,3-diones was developed. With suitable and straightforward reaction condition adjustments, the C–H bond functionalization of diverse aryl imidates with cyclic 1,3-diones occurred smoothly and precisely at room temperature. Accompanied by different directing group transformations, a series of corresponding aryl nitriles, hydrophenanthridin-1(2H)-ones, spiro isoindoles, or hydrophenanthridine-1,6(2H,5H)-diones were synthesized in good yields to provide a rational directing group utilization strategy for the Rh(III)-catalyzed C(sp²)–H bond activation. Control experiments and primary mechanistic studies revealed that solvent effects and functional group electronic effects might influence the reaction’s selectivity.

中文翻译：

环状 1,3-二酮对芳基亚胺酸酯的可调 Rh(III) 催化 C(sp2)–H 键官能化：定向基团的战略使用

开发了一种可调节的 Rh(III) 催化的亚胺酸芳基酯与环状 1,3-二酮的 C(sp ² )-H 键官能化。通过适当且直接的反应条件调整，各种芳基亚胺酸酯与环状1,3-二酮的C-H键官能化在室温下顺利且精确地发生。伴随不同的导向基团转化，以良好的收率合成了一系列相应的芳基腈、氢菲啶-1(2 H )-酮、螺异吲哚或氢菲啶-1,6(2 H ,5 H )-二酮，提供了Rh(III) 催化的 C(sp ² )–H 键活化的合理导向基团利用策略。对照实验和主要机理研究表明，溶剂效应和官能团电子效应可能会影响反应的选择性。

更新日期：2024-09-06

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