有机介质使n -芳基-2-碘苯酰胺/ n -磺酰-2-碘苯胺的电化学1,4-芳基迁移接近双芳基

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-05-13 DOI:10.1039/d5qo00484e

Xiao-Qing Xie, Li-Tong Xiao, Wei Zhou, Yanli Wu, Haixin Ding, Ruchun Yang, Xian-Rong Song, Mu-Jia Luo, Qiang Xiao

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引用次数: 0

摘要

本文描述了以催化量的9-溴菲作为氧化还原介质促进n -芳基-2-碘苯酰胺/ n -磺酰-2-碘苯胺的电还原自由基1,4-芳基迁移。在温和的条件下，该工艺在未分裂的细胞中顺利进行，在没有任何过渡金属催化剂、化学还原剂或牺牲阳极的情况下，以中等到良好的产量生产出多种结构通用的双芳基。初步的机理研究表明，通过阴极单电子还原生成芳基自由基是至关重要的，包括分子内5-外三螺旋环化、C-N键裂解和氢原子提取。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Organo-mediator enabled electrochemical 1,4-aryl migration of N-aryl-2-iodobenzamides/N-sulfonyl-2-iodoanilines to access biaryls

Herein, an electroreductive radical 1,4-aryl migration of N-aryl-2-iodobenzamides/N-sulfonyl-2-iodoanilines promoted by catalytic amounts of 9-bromophenanthrene as redox mediator is described. This protocol proceeds smoothly in an undivided cell under mild conditions, producing a wide range of structurally versatile biaryls in moderate to good yields without any transition metal catalysts, chemical reductants, or sacrificial anodes. Preliminary mechanistic studies revealed that the generation of aryl radical via cathodic single-electron reduction is crucial, with sequential intramolecular 5-exo-trig spirocyclization, C-N bond cleavage, and hydrogen atom abstraction.

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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.