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Copper‐Catalyzed Direct Thiolation of Pentafluorobenzene with Diaryl Disulfides or Aryl Thiols by C–H and C–F Bond Activation
Author(s) -
Yu Chuanming,
Zhang Cuiling,
Shi Xiangjun
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101676
Subject(s) - chemistry , aryl , catalysis , copper , medicinal chemistry , polymer chemistry , organic chemistry , stereochemistry , alkyl
Abstract A Cu‐catalyzed cross‐coupling reaction of diaryl disulfides or aryl thiols with pentafluorobenzene using CuBr as the catalyst, t BuOLi or t BuOK as the base in DMSO at 60 °C under an O 2 atmosphere was investigated. The corresponding bisarylthiolation products were obtained in moderate to good yields by C–H bond and C–F bond activation. When 1,10‐phenanthroline · H 2 O 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 throughC–H bond and C–F bond activation.