静电相互作用辅助的区域特异性和无氧化剂的[4+2]环化由RhIII催化的C−H键激活实现

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-07-23 DOI:10.1039/d5qo00765h

Xiaogang Cui, Renyi Diao, Rui Ma, Minglong Zhang, Chuan Zhu, Cheng-Qiang Wang, Chao Feng

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引用次数: 0

摘要

以N-tosylamide和羧基为导向基团，建立了一种rhiii催化的分子间[4+2]环化反应。利用易获得的丙炔三酸铵盐作为偶联伙伴，可以在无氧化剂的条件下高效地合成异喹诺酮类药物和异香豆素。此外，该方法的特点是易于获得基材和广泛的功能耐受性。此外，初步的控制实验表明，静电相互作用在实现该转化中观察到的反向区域选择性中起着关键作用，使其与先前的相关研究不同。

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Electrostatic interaction-assisted regiospecific and oxidant free [4+2] annulation enabled by RhIII catalyzed C−H bond activation

A RhIII-catalyzed intermolecular [4+2] annulation reaction, employing N-tosylamide and carboxyl as the directing groups, has been developed herein. The utilization of readily accessible propargylic aminium triflate salts as coupling partners enables a highly efficient strategy for the regiospecific synthesis of isoquinolones and isocoumarins under oxidant-free conditions. In addition, this method is characterized by its facile substrates availability and broad functionality tolerance. Furthermore, preliminary control experiments reveal that electrostatic interaction plays a pivotal role in achieving the reversed regioselectivity observed in this transformation, setting it apart from previous related studies.

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.