Arenethiolate-catalyzed Caryl−F bond activation: Synthesis of oxindoles

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC Organic Chemistry Frontiers Pub Date : 2024-12-30 DOI:10.1039/d4qo01888e

Shengyun Liu, Mingying Li, Wei Xiao, Jie Wu

引用次数: 0

Abstract

Single electron reduction of the Caryl−F bond is quite challenging due to its high reduction potential. Herein, we report an arenethiolate-catalyzed single electron reduction of the Caryl−F bond to access oxindoles. A variety of oxindoles are provided in moderate to excellent yields through a single electron reduction/cyclization/single electron oxidation process. Furthermore, the 1,5-HAT of inert C−H could be achieved with this method. A plausible pathway with the arenethiolate as a SET catalyst is proposed on the basis of mechanistic 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.