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

Nan Ding; Zhi Li

doi:10.1055/a-2123-7565

Synlett, Table of Contents

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 ∗

Abstract

All articles of this category

Dedicated to the 80^th 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

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References

References and Notes
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