Efficient electrochemical synthesis of robust, densely functionalized water soluble quinones

Gerken, James B.; Stamoulis, Alexios; Suh, Sung-Eun; Fischer, Nicholas D.; Kim, Yeon J.; Guzei, I A.; Stahl, Shannon S.

doi:10.1039/C9CC08878D

Efficient electrochemical synthesis of robust, densely functionalized water soluble quinones

Journal Article · Fri Jan 24 23:00:00 EST 2020 · Chemical Communications

DOI:https://doi.org/10.1039/C9CC08878D· OSTI ID:1728686

Gerken, James B. ^[1]; Stamoulis, Alexios ^[1]; Suh, Sung-Eun ^[1]; Fischer, Nicholas D. ^[1]; Kim, Yeon J. ^[1]; Guzei, I A. ^[2]; Stahl, Shannon S. ^[1]

University of Wisconsin-Madison
unknown

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. Financial support for this work was provided by the Center for Molecular Electrocatalysis, an Energy Frontier Research Center funded by the US Department of Energy, Office of Science, Office of Basic Energy Sciences, and by the Wisconsin Alumni Research Foundation (WARF) through the WARF Accelerator Program. NMR spectroscopy facilities were partially supported by NSF CHE-0342998, NSF CHE-1048642, a UW Madison Instructional Laboratory Modernization Award, a gift from Paul J. and Margaret M. Bender, and by NIH S10 OD012245. Mass spectrometry equipment was partially supported by NIH 1S10 OD020022-1.

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Center for Molecular Electrocatalysis (CME); Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: AC05-76RL01830

OSTI ID:: 1728686

Report Number(s):: PNNL-SA-150205

Journal Information:: Chemical Communications, Journal Name: Chemical Communications Journal Issue: 8 Vol. 56

Country of Publication:: United States

Language:: English

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