Hydrogen Bond-Controlled Site-Selective C(sp^3)–H Alkylation of Sulfonanilides

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  • Sekine, Kohei
    Institute for Materials Chemistry and Engineering, Kyushu University Department of Interdisciplinary Engineering Sciences, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
  • Jiang, Hui
    Department of Interdisciplinary Engineering Sciences, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
  • Kuninobu, Yoichiro
    Institute for Materials Chemistry and Engineering, Kyushu University Department of Interdisciplinary Engineering Sciences, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University

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Other Title
  • Hydrogen Bond-Controlled Site-Selective C(sp<sup>3</sup>)–H Alkylation of Sulfonanilides
Published
2025-02-27
Resource Type
journal article
Rights Information
  • This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © 2025 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.5c00027.
DOI
  • 10.1021/acs.joc.5c00027
Publisher
American Chemical Society (ACS)

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Description

We successfully developed a decatungstate-catalyzed benzylic C(sp^3)–H alkylation of sulfonanilides by utilizing the hydrogen bond between the sulfonamide group of the substrates and decatungstate photocatalysts. Using this catalytic system, site-selective C(sp^3)–H alkylation was achieved at the benzylic position near the sulfonamide group.

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