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Efficient electrochemical synthesis of robust, densely functionalized water soluble quinones

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Abstract

Conjugate addition of thiols to benzoquinones has been coupled to in situ electrochemical oxidation of the resulting hydroquinone to enable full substitution of quinone C–H bonds. The sulfonated thioether-substituted quinones exhibit high solublity and stability in aqueous solution and have redox potentials ranging from 440–750 mV vs. SHE. The electrosynthetic protocol is effective on >100 g scale.

Graphical abstract: Efficient electrochemical synthesis of robust, densely functionalized water soluble quinones

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Article information


Submitted
13 Nov 2019
Accepted
18 Dec 2019
First published
18 Dec 2019

Chem. Commun., 2020, Advance Article
Article type
Communication

Efficient electrochemical synthesis of robust, densely functionalized water soluble quinones

J. B. Gerken, A. Stamoulis, S. Suh, N. D. Fischer, Y. J. Kim, I. A. Guzei and S. S. Stahl, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC08878D

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