Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 10, Pages 1953-1959Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101676
Keywords
Copper; Sulfur; Fluorine; C-H activation; C-F activation; Cross-cou-pling
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Funding
- National Natural Science Foundation of China [20876147]
- Zhejiang Natural Science Foundation [Y4090346]
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A Cu-catalyzed cross-coupling reaction of diaryl disulfides or aryl thiols with pentafluorobenzene using CuBr as the catalyst, tBuOLi or tBuOK as the base in DMSO at 60 degrees C under an O2 atmosphere was investigated. The corresponding bisarylthiolation products were obtained in moderate to good yields by CH bond and CF bond activation. When 1,10-phenanthroline center dot H2O and DDQ were added to the above system, monoarylthiolation products, with/without bisarylthiolation products, could be isolated in moderate yields. A plausible mechanism for these transformations was given. Thus, it represents a method for the synthesis of polyfluorinated diaryl sulfides and polyfluorinated triarylbisulfides throughCH bond and CF bond activation.
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