Palladium-catalyzed addition reactions of diaryl disulfides and diselenides to terminal alkynes can proceed smoothly in room temperature ionic liquid, 1-butyl-3-methylimidazoliumhexafluorophosphate ([bmim][PF6]), to afford the corresponding (Z)-1,2-bis(arylthio)-1-alkenes or (Z)-1,2-bis(arylseleno)-1-alkenes in excellent yields. Our system not only avoids the use of highly toxic benzene or toluene as a solvent but also solves the basic problem of palladium catalyst reuse.
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Cai et al. (2007) studied this question.