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Synlett
DOI: 10.1055/a-2720-9415
Letter

Alkoxy Group-Boosted Internal Redox Reaction: Application to Benzylic Hydride Shift/Cyclization of Electron-Deficient Aromatic Rings

Authors

  • Mizuki Katagiri

    1   Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Japan

  • Tomoko Kawasaki-Takasuka

    2   Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology Faculty of Engineering Graduate School of Engineering, Koganei, Japan (Ringgold ID: RIN98293)
    2   Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology Faculty of Engineering Graduate School of Engineering, Koganei, Japan (Ringgold ID: RIN98293)

  • Keiji Mori 

    1   Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Japan
Further Information
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We report a C(sp3)–H bond functionalization at the benzylic position of electron-deficient aromatic rings, considered a challenging transformation in hydride shift mediated C(sp3)–H bond functionalization chemistry. The key to achieving the reaction was the employment of substrates having a methoxy group at the benzylic position. The methoxy group was easily eliminated from the cyclized adducts by treating with a strong Brønsted acid, such as TfOH. A one-pot operation of two processes, C(sp3)–H bond functionalization and MeOH elimination, was also accomplished. Synthetic utility of the present method was well showcased by derivatization from the obtained dihydronaphthalenes.



Publication History

Received: 11 September 2025

Accepted after revision: 10 October 2025

Accepted Manuscript online:
10 October 2025

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