PNNL

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. 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.