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

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

Publication History

Received: 30 April 2023

Accepted after revision: 05 July 2023

Accepted Manuscript online:
05 July 2023

Article published online:
29 August 2023

• References and Notes

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