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  1. Article ; Online: Halogen-Bond-Promoted Direct Cross-Coupling of Trifluoromethylated Alkyl Bromides with Coumarins/Quinolinones: Unraveling Trifluoromethyl Effects.

    Guo, Peng / Pu, Guoliang / Wang, Gairong / Zeng, Lin-Yuan / Li, Wei-Piao / Li, Xuefei / Zhou, Pan-Pan / He, Chun-Yang

    Organic letters

    2024  Volume 26, Issue 15, Page(s) 3097–3102

    Abstract: This study introduces a novel approach involving XB-mediated cross-coupling of α-trifluoromethylated alkyl bromides with coumarins and quinolinones under visible light irradiation. Both density functional theory (DFT) calculations and experimental ... ...

    Abstract This study introduces a novel approach involving XB-mediated cross-coupling of α-trifluoromethylated alkyl bromides with coumarins and quinolinones under visible light irradiation. Both density functional theory (DFT) calculations and experimental studies converge to suggest that the noncovalent interaction between alkyl bromides and DMAP, intensified by the α-trifluoromethyl group, plays a pivotal role in facilitating this chemoselective reaction.
    Language English
    Publishing date 2024-04-04
    Publishing country United States
    Document type Journal Article
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.4c00717
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article: Visible-light promoted cross-coupling of ethyl iododifluoroacetate with silyl enol ethers for the synthesis of β-fluoroenones via noncovalent interactions

    Huang, Qi-Ping / Li, Wei-Piao / Li, Rui / Zhao, Liang / Wang, Hao-Yang / Li, Xuefei / Wang, Pan / He, Chun-Yang

    Tetrahedron letters. 2022 Apr. 04,

    2022  

    Abstract: Monofluoroalkene is an important motif in drug development as it serves as an ideal mimic of peptide amide bond. Herein, a visible light promoted cross-coupling of ethyl iododifluoroacetate with silyl enol ethers for the synthesis of β-fluoroenones is ... ...

    Abstract Monofluoroalkene is an important motif in drug development as it serves as an ideal mimic of peptide amide bond. Herein, a visible light promoted cross-coupling of ethyl iododifluoroacetate with silyl enol ethers for the synthesis of β-fluoroenones is presented. The transformation was mediated by non-covalent interactions, in which solvent acts as an electron donor. This protocol can also be applied for the synthesis of α, β-polyfluoroenones. The advantages of this protocol are mild reaction conditions, excellent functional group tolerance, synthetic flexibility, and operational simplicity.
    Keywords cross-coupling reactions ; drug development ; enols ; light ; peptides ; solvents
    Language English
    Dates of publication 2022-0404
    Publishing place Elsevier Ltd
    Document type Article
    Note Pre-press version
    ZDB-ID 204287-3
    ISSN 1873-3581 ; 0040-4039
    ISSN (online) 1873-3581
    ISSN 0040-4039
    DOI 10.1016/j.tetlet.2022.153782
    Database NAL-Catalogue (AGRICOLA)

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