Aggregation-induced C–C bond formation on an electrode driven by the surface tension of water

Electrochemical organic synthesis is typically conducted in organic media. The solvent and related supporting electrolytes negatively affect the greenness of electrosynthesis. In this work, with 100% water used as the solvent, we realize aggregation-driven electrochemical radical cross coupling of unsaturated compounds driven by water tension. A key finding is that aggregation of the substrate at the electrode confined the radical intermediate and prevented side reactions, thus providing a way to regulate radical reactions in addition to their native properties. The reaction provides up to 90% yields with almost quantitative chemoselectivity. The pure water system readily yields the products via cold filtration, and the solvent is recycled repeatedly. In particular, the life span of the radical species generated in the reaction increase significantly because of the confined environment in the aggregation state. The greenness of this protocol is further enhanced with readily separation of product from media using cooling and filtration.

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Publication Details

Journal
Nature Communications
Published
2024-08-30
DOI
https://doi.org/10.1038/s41467-024-52042-w
Citations
5
Primary Topic
Advanced Chemical Sensor Technologies
Type
article
Field-Weighted Citation Impact
0.92

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article

Aggregation-induced C–C bond formation on an electrode driven by the surface tension of water

Xu Cheng, Mengfan Li
5 citations
Nature Communications
Advanced Chemical Sensor Technologies
0.92
article

Aggregation-induced C–C bond formation on an electrode driven by the surface tension of water

Xu Cheng, Mengfan Li
article en
5 citations

Abstract

Electrochemical organic synthesis is typically conducted in organic media. The solvent and related supporting electrolytes negatively affect the greenness of electrosynthesis. In this work, with 100% water used as the solvent, we realize aggregation-driven electrochemical radical cross coupling of unsaturated compounds driven by water tension. A key finding is that aggregation of the substrate at the electrode confined the radical intermediate and prevented side reactions, thus providing a way to regulate radical reactions in addition to their native properties. The reaction provides up to 90% yields with almost quantitative chemoselectivity. The pure water system readily yields the products via cold filtration, and the solvent is recycled repeatedly. In particular, the life span of the radical species generated in the reaction increase significantly because of the confined environment in the aggregation state. The greenness of this protocol is further enhanced with readily separation of product from media using cooling and filtration.

Nature CommunicationsVol. 15(1)
Institute of Chemistry (CN), Nanjing University (CN)
National Science Foundation, National Natural Science Foundation of China
Clean water and sanitation
Openalex Percentile: Top 28%
Advanced Chemical Sensor Technologies
0.92
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Aggregation-induced C–C bond formation on an electrode driven by the surface tension of water — Xu Cheng, Mengfan Li · Nature Communications (2024) | TGRS Research Map | TGRS