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Electronic Influences on the Dynamic Range of Photoswitchable Dithienylethene–Thiourea Organocatalysts

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    Electronic Influences on the Dynamic Range of Photoswitchable Dithienylethene–Thiourea Organocatalysts
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2023, 88, 7, 4372–4378
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    https://doi.org/10.1021/acs.joc.2c02987
    Published March 20, 2023
    Copyright © 2023 American Chemical Society
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    Abstract

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    Thiourea-based organocatalysts bearing a photoswitchable dithienylethene (DTE) core and a wide range of substituents were prepared and extensively tested for their ability to accelerate the Michael reaction between acetylacetone and trans-β-nitrostyrene. There is a strong correlation between the Hammett parameter of the modulating groups and catalytic activity following UV irradiation. Electron-withdrawing groups afford the largest reactivity difference between the catalysts in their ring-open form and their ring-closed isomer, with evidence for electronic coupling between the two halves in both oDTE and cDTE.

    Copyright © 2023 American Chemical Society

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    • Detailed synthetic procedures; spectroscopic and chromatographic characterization of organocatalysts; and reaction kinetics data (PDF)

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    Cited By

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    This article is cited by 1 publications.

    1. Anastasiia Sherstiuk, Agustí Lledós, Peter Lönnecke, Jordi Hernando, Rosa María Sebastián, Evamarie Hey-Hawkins. Dithienylethene-Based Photoswitchable Phosphines for the Palladium-Catalyzed Stille Coupling Reaction. Inorganic Chemistry 2024, 63 (17) , 7652-7664. https://doi.org/10.1021/acs.inorgchem.3c04423
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2023, 88, 7, 4372–4378
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.2c02987
    Published March 20, 2023
    Copyright © 2023 American Chemical Society
    Request reuse permissions

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