Organic Letters · 2019 · 25 citations · 58 references
Natural SciencesChemistryCatalysisOrganic ChemistryMetal SulfidesArene FunctionalizationHydrolysis PathwaysHydrolysis ReactionsRoom-temperature SynthesisThiol ChemistryThiol Functionalization
Cu-mediated C-H thioetherification of arenes with ethylene sulfide has been developed using a readily removable directing group. The reaction proceeded at room temperature, and a variety of sensitive functional groups including chloro, bromo, and vinyl were well tolerated. The thiolated products could be converted to the seven-membered benzoxathiepinones derivatives by a sequence of hydrolysis-lactonization reactions.
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Alison M. Suess, Mehmed Z. Ertem, Christopher J. Cramer et al. · Journal of the American Chemical Society · 2013 · 426 citations