Journal
CHEMICAL COMMUNICATIONS
Volume 56, Issue 8, Pages 1199-1202Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9cc08878d
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Funding
- Center for Molecular Electrocatalysis, an Energy Frontier Research Center - US Department of Energy, Office of Science, Office of Basic Energy Sciences
- Wisconsin Alumni Research Foundation (WARF)
- NSF [CHE-1048642, CHE-0342998]
- UW Madison Instructional Laboratory Modernization Award
- NIH [1S10 OD020022-1, S10 OD012245]
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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.
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