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Synlett 2023; 34(20): 2417-2422
DOI: 10.1055/a-2123-7565
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Special Issue Dedicated to Prof. Hisashi Yamamoto

Acid-Catalyzed [4+1]-Dearomatization Spiroannulation of Hydroquinones and Naphthols

Nan Ding
,
Zhi Li  ∗
Financial support for this work was generously provided by ShanghaiTech University.
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Dedicated to the 80th birthday of Professor Hisashi Yamamoto.

Abstract

Acid-catalyzed [4+1]-dearomatization spiroannulation reactions of electron-rich hydroquinone and naphthol derivatives were demonstrated as convenient methods to access spirocyclic cyclohexadienone derivatives. The Lewis acid Bi(OTf)3 exhibited the best catalytic performance when a 1,2-dialkynylbenzene was used as the electrophile for the spiroannulation, whereas the Brønsted acid benzene-1,2-disulfonic acid was the best catalyst when 2-ethynylbenzylic esters were used as electrophiles. Most of the reaction conditions are mild, efficient, and simple to operate.

Key words

acid catalysis - dearomatization - spiroannulation - hydroquinones - naphthols - diyne

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2123-7565.
  • Supporting Information


Publication History

Received: 30 April 2023

Accepted after revision: 05 July 2023

Accepted Manuscript online:
05 July 2023

Article published online:
29 August 2023

© 2023. Thieme. All rights reserved

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