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Cobalt Bromide-Catalyzed Negishi-Type Cross-Coupling of Amides
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    Cobalt Bromide-Catalyzed Negishi-Type Cross-Coupling of Amides
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    Organic Letters

    Cite this: Org. Lett. 2022, 24, 14, 2778–2782
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    https://doi.org/10.1021/acs.orglett.2c00940
    Published April 5, 2022
    Copyright © 2022 American Chemical Society

    Abstract

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    Herein, we describe a novel Negishi-type cross-coupling of amides employing only cobalt bromide salt as the catalyst. This original reaction is highly tolerant to various glutarimide amides as well as organozinc coupling partners. These conditions also allow the performance of the cross-coupling reaction in an eco-compatible solvent such as ethyl acetate on a large scale.

    Copyright © 2022 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.2c00940.

    • General experimental details, optimization of reactions, experimental procedure, characterization data, and NMR spectral data (PDF)

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    CCDC 2141647 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    Cited By

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    This article is cited by 6 publications.

    1. Muzammil, Ameer Fawad Zahoor, Bushra Parveen, Sadia Javed, Rabia Akhtar, Shaheera Tabassum. Recent developments in the chemistry of Negishi coupling: a review. Chemical Papers 2024, 78 (6) , 3399-3430. https://doi.org/10.1007/s11696-024-03369-7
    2. A. Haupt, I. Fleischer. Coupling Reactions Between sp3 and sp2 Carbon Centers. 2024https://doi.org/10.1016/B978-0-323-96025-0.00070-3
    3. Myeong Seong Park, Karthik Rajan Rajamanickam, Kwang Ho Song, Sunwoo Lee. 1,3‐Diketone‐Mediated Synthesis of Symmetrical Aryl Imides from Activated Amides. Asian Journal of Organic Chemistry 2023, 12 (12) https://doi.org/10.1002/ajoc.202300469
    4. Pulluparambil Xavier Thresia Rinu, Rose Mary Philip, Gopinathan Anilkumar. Low-cost transition metal catalysed Negishi coupling: an update. Organic & Biomolecular Chemistry 2023, 21 (32) , 6438-6455. https://doi.org/10.1039/D3OB00784G
    5. Chengwei Liu, Michal Szostak. Amide N–C Bond Activation: A Graphical Overview of Acyl and Decarbonylative Coupling. SynOpen 2023, 07 (01) , 88-101. https://doi.org/10.1055/a-2035-6733
    6. Corinne Gosmini, Mengyu Gao. Co-catalyzed C–C Coupling Reactions with Csp2 Electrophiles. 2023, 145-179. https://doi.org/10.1007/3418_2023_89

    Organic Letters

    Cite this: Org. Lett. 2022, 24, 14, 2778–2782
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.2c00940
    Published April 5, 2022
    Copyright © 2022 American Chemical Society

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