Electrochemical Dearomatizing Spirolactonization and Spiroetherification of Naphthols and Phenols

Abstract

An electrochemical oxidative ortho-dearomatization of naphthols and phenols with an intramolecular C–O bond formation has been developed. A careful optimization of the reaction parameters allowed for the application of free phenols as the starting materials, in contrast to the existing alternative procedures necessitating aryl methyl ether substrates. The reaction delivers an array of spirolactones and spiroethers in yields up to 97%, under simple experimental conditions: in a constant current mode, using an undivided cell, and without an inert atmosphere. The method avoids using catalysts or stoichiometric oxidants (e.g., hypervalent iodine reagents), generating hydrogen as the sole byproduct.

Key words

electrosynthesis - dearomatization - oxidation - spirolactonization - spiroetherification - naphthols - phenols

Publication History

Received: 23 June 2023

Accepted after revision: 13 July 2023

Accepted Manuscript online:
13 July 2023

Article published online:
05 September 2023

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