Overcoming Selectivity Trade-Offs in Alkene Azidodifluoroalkylation: An Enlightening Synergistic Catalytic Approach

Recent advances in dual catalysis involving biomimetic conversion strategies that utilize radical ligand transfer (RLT) often rely on large doses of precious metal additives. The role of these additives within the mechanism remains ambiguous, leading to complex reaction conditions, uncertain pathways, and increased costs. These challenges complicate the study of the reaction process and are accompanied by potential safety risks. To address these issues, azide salt was used as an alternative to TMSN<sub>3</sub>. This replacement not only avoids the drawbacks associated with almost parallel research on alkene azidodifluoroalkylation but also eliminates the need for ligands. Comparative analysis indicates that existing biomimetic synergistic catalysis strategies require Ag<sub>2</sub>CO<sub>3</sub> additives to enhance selectivity in alkene difunctionalization reactions, highlighting the superior simplicity, environmental friendliness, and operational ease of our developed synergistic catalysis strategy. Furthermore, under the guidance of our proposed mechanism, an alkene azidosulfonation was designed, validating the innovative and practical applicability of our synergistic catalysis approach.

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Publication Details

Journal
Organic Letters
Published
2024-12-23
DOI
https://doi.org/10.1021/acs.orglett.4c04015
Citations
2
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.42

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article

Overcoming Selectivity Trade-Offs in Alkene Azidodifluoroalkylation: An Enlightening Synergistic Catalytic Approach

Ling‐Guo Meng, Yue Ren, Zhao-Juan Wu, Ziyang Li
2 citations
Organic Letters
Fluorine in Organic Chemistry
0.42
article

Overcoming Selectivity Trade-Offs in Alkene Azidodifluoroalkylation: An Enlightening Synergistic Catalytic Approach

Ling‐Guo Meng, Yue Ren, Zhao-Juan Wu, Ziyang Li
article en
2 citations

Abstract

Recent advances in dual catalysis involving biomimetic conversion strategies that utilize radical ligand transfer (RLT) often rely on large doses of precious metal additives. The role of these additives within the mechanism remains ambiguous, leading to complex reaction conditions, uncertain pathways, and increased costs. These challenges complicate the study of the reaction process and are accompanied by potential safety risks. To address these issues, azide salt was used as an alternative to TMSN<sub>3</sub>. This replacement not only avoids the drawbacks associated with almost parallel research on alkene azidodifluoroalkylation but also eliminates the need for ligands. Comparative analysis indicates that existing biomimetic synergistic catalysis strategies require Ag<sub>2</sub>CO<sub>3</sub> additives to enhance selectivity in alkene difunctionalization reactions, highlighting the superior simplicity, environmental friendliness, and operational ease of our developed synergistic catalysis strategy. Furthermore, under the guidance of our proposed mechanism, an alkene azidosulfonation was designed, validating the innovative and practical applicability of our synergistic catalysis approach.

Organic LettersVol. 27(1)
Huaibei Normal University (CN)
National Natural Science Foundation of China, Anhui Provincial Department of Education
Openalex Percentile: Top 40%
Fluorine in Organic Chemistry
0.42
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