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Exploiting the Bis-Nucleophilicity of α-Aminoboronates: Copper-Catalyzed, Intramolecular Aminoalkylations of Bromobenzoyl Chlorides

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    Exploiting the Bis-Nucleophilicity of α-Aminoboronates: Copper-Catalyzed, Intramolecular Aminoalkylations of Bromobenzoyl Chlorides
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    Department of Process Chemistry, Merck Sharp and Dohme Ltd., Hertford Road, Hoddesdon EN11 9BU, United Kingdom
    *E-mail: [email protected] or [email protected]
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    Organic Letters

    Cite this: Org. Lett. 2016, 18, 8, 1848–1851
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    https://doi.org/10.1021/acs.orglett.6b00586
    Published March 28, 2016
    Copyright © 2016 American Chemical Society
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    Abstract

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    α-Aminoboronate salts are interesting examples of heteroatomic species containing adjacent nucleophilic centers. We have developed an acylation/arylation reaction using 2-bromobenzoyl chlorides as bis-electrophiles that harnesses the nucleophilicity of both positions, leading to isoindolinones. The reactions proceed under mild conditions via an intramolecular, Cu-catalyzed sp3–sp2 coupling, giving products in up to 95% yield. These conditions enable arylation of α,α-disubstituted aminoboronates, which are difficult to accomplish using methods based on less abundant and more expensive transition metals.

    Copyright © 2016 American Chemical Society

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    • Experimental details and characterization data for preparation of isoindolinones and precursor aminoboronate salts(PDF)

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    This article is cited by 17 publications.

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    2. Andrés Borja-Miranda, Fabiola Valencia-Villegas, J. Armando Lujan-Montelongo, Luis A. Polindara-García. Synthesis of Polysubstituted Isoindolinones via Radical Cyclization of 1,3-Dicarbonyl Ugi-4CR Adducts Using Tetrabutylammonium Persulfate and TEMPO. The Journal of Organic Chemistry 2021, 86 (1) , 929-946. https://doi.org/10.1021/acs.joc.0c02441
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    11. Andrej Šterman, Janez Košmrlj, Nina Žigart, Stanislav Gobec, Izidor Sosič, Zdenko Časar. Catalytic Approach to Diverse α‐Aminoboronic Acid Derivatives by Iridium‐Catalyzed Hydrogenation of Trifluoroborate‐Iminiums. Advanced Synthesis & Catalysis 2021, 363 (9) , 2396-2402. https://doi.org/10.1002/adsc.202001350
    12. Risto Savela, Carolina Méndez‐Gálvez. Isoindolinone Synthesis via One‐Pot Type Transition Metal Catalyzed C−C Bond Forming Reactions. Chemistry – A European Journal 2021, 27 (17) , 5344-5378. https://doi.org/10.1002/chem.202004375
    13. Yukako Yoshinaga, Takeshi Yamamoto, Michinori Suginome. Stereoinvertive C–C Bond Formation at the Boron‐Bound Stereogenic Centers through Copper‐Bipyridine‐Catalyzed Intramolecular Coupling of α‐Aminobenzylboronic Esters. Angewandte Chemie 2020, 132 (18) , 7318-7322. https://doi.org/10.1002/ange.201914864
    14. Yukako Yoshinaga, Takeshi Yamamoto, Michinori Suginome. Stereoinvertive C–C Bond Formation at the Boron‐Bound Stereogenic Centers through Copper‐Bipyridine‐Catalyzed Intramolecular Coupling of α‐Aminobenzylboronic Esters. Angewandte Chemie International Edition 2020, 59 (18) , 7251-7255. https://doi.org/10.1002/anie.201914864
    15. Andrej Šterman, Izidor Sosič, Stanislav Gobec, Zdenko Časar. Synthesis of aminoboronic acid derivatives: an update on recent advances. Organic Chemistry Frontiers 2019, 6 (16) , 2991-2998. https://doi.org/10.1039/C9QO00626E
    16. Byeong Hyo Kim, Byung Min Lee, Eungyung Kim, Mingyeong Jeong. One-Pot Synthesis of Isoindolin-1-ones from Nitroarenes and o-Phthalaldehyde via Indium-Mediated Reductive Condensation Reactions. HETEROCYCLES 2018, 96 (10) , 1759. https://doi.org/10.3987/COM-18-13968
    17. Aaron M. Dumas, Adrian J. Sieradzki, Liam J. Donnelly. ChemInform Abstract: Exploiting the Bis-Nucleophilicity of α-Aminoboronates: Copper-Catalyzed, Intramolecular Aminoalkylations of Bromobenzoyl Chlorides.. ChemInform 2016, 47 (34) https://doi.org/10.1002/chin.201634111
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    Organic Letters

    Cite this: Org. Lett. 2016, 18, 8, 1848–1851
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.6b00586
    Published March 28, 2016
    Copyright © 2016 American Chemical Society
    Request reuse permissions

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