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Transition-Metal-Free C–N Cross-Coupling Enabled by a Multifunctional Reagent

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    Transition-Metal-Free C–N Cross-Coupling Enabled by a Multifunctional Reagent
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2024, 146, 10, 6476–6480
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    https://doi.org/10.1021/jacs.4c00871
    Published March 4, 2024
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    Abstract

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    We report the design and development of a transition-metal-free cross-coupling reaction of phenols and primary amines using a simple and readily available multifunctional reagent. The reactions work by induced proximity and electronic activation of both the nucleophile and the electrophile for net dehydrative C–N coupling reactions. Notably, the reactions do not involve the use of a transition metal for C–N bond formation, preactivation of the phenol electrophile, or exclusion of air or moisture. The mild conditions tolerate a broad range of functional groups and allow for this to be applied to the late-stage functionalization of complex substrates with a wide scope of coupling partners.

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    Cited By

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    This article is cited by 2 publications.

    1. Matthew C. Carson, Cindy R. Liu, Yaning Liu, Marisa C. Kozlowski. Amination of Phenols and Halophenols via Pyridinium–Iridium Dual Photocatalysis. ACS Catalysis 2024, 14 (16) , 12173-12180. https://doi.org/10.1021/acscatal.4c02797
    2. Kai Chen, Hang Shi. Nucleophilic Aromatic Substitution of Halobenzenes and Phenols with Catalysis by Arenophilic π Acids. Accounts of Chemical Research 2024, 57 (15) , 2194-2206. https://doi.org/10.1021/acs.accounts.4c00327
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2024, 146, 10, 6476–6480
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.4c00871
    Published March 4, 2024
    Copyright © 2024 American Chemical Society
    Request reuse permissions

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