Ni-Catalyzed Electro-Reductive Cross-Electrophile Couplings of Alkyl Amine-Derived Radical Precursors with Aryl Iodides.

IF 3.3 2区 化学 Q1 CHEMISTRY, ORGANIC The Journal of Organic Chemistry Pub Date : 2024-11-15 Epub Date: 2023-05-23 DOI:10.1021/acs.joc.3c00859
Lars J Wesenberg, Alessandra Sivo, Gianvito Vilé, Timothy Noël
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Abstract

In recent years, the "Escape-from-Flatland" trend has prompted the synthetic community to develop a set of cross-coupling strategies to introduce sp3-carbon-based fragments in organic compounds. This study presents a novel nickel-catalyzed electrochemical methodology for reductive cross-electrophile coupling. The method enables C(sp2)-C(sp3) linkages using inexpensive amine-derived radical precursors and aryl iodides. The use of electrochemistry as a power source reduces waste and avoids chemical reductants, making this approach a more sustainable alternative to traditional cross-coupling methods.

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镍催化烷基胺衍生自由基前体与芳基碘化物的电诱导交叉亲电偶联。
近年来,"逃离平原 "的趋势促使合成界开发出一套交叉偶联策略,在有机化合物中引入以 sp3 碳为基础的片段。本研究介绍了一种新型的镍催化电化学还原交叉亲电偶联方法。该方法利用廉价的胺衍生自由基前体和芳基碘化物实现了 C(sp2)-C(sp3)连接。使用电化学作为动力源可减少浪费并避免使用化学还原剂,从而使这种方法成为传统交叉偶联方法的一种更具可持续性的替代方法。
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来源期刊
The Journal of Organic Chemistry
The Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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