- Organocatalyzed Fluoride Metathesis
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A new organocatalyzed fluoride metathesis reaction between fluoroarenes and carbonyl derivatives is reported. The reaction exchanges fluoride (F-) and alternate nucleophiles (OAc-, OCO2R-, SR-, Cl-, CN-, NCS-). The approach provides a conceptually novel route to manipulate the fluorine content of organic molecules. When the fluorination and defluorination steps are combined into a single catalytic cycle, a byproduct free and 100% atom-efficient reaction can be achieved.
- Mulryan, Daniel,White, Andrew J. P.,Crimmin, Mark R.
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supporting information
p. 9351 - 9355
(2020/11/30)
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- Palladium(II)/Copper(II)-Catalyzed C–H Sulfidation or Selenation of Arenes Leading to Unsymmetrical Sulfides and Selenides
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A novel palladium(II)/copper(II)-catalyzed sulfidation of the C–H bond in electron-rich arenes and in pentafluorobenzene with disulfides was developed. This catalytic system can be used to efficiently produce various types of either unsymmetrical aryl sulfides or alkyl aryl sulfides. The present protocol could also be applied to the direct preparation of unsymmetrical aryl selenides via C–H selenation.
- Nishino, Kota,Tsukahara, Shouya,Ogiwara, Yohei,Sakai, Norio
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supporting information
p. 1588 - 1593
(2019/02/09)
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- Synthesis of unsymmetrical polyfluorinated diaryl sulfides by rhodium-catalyzed aryl exchange reaction
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RhH(PPh3)4 and 1,2-bis(diphenylphosphino)benzene (dppBz) catalyze the aryl exchange reaction of polyfluorinated diaryl sulfides. By employing these catalysts, unsymmetrical polyfluorinated diaryl sulfides are synthesized by the react
- Arisawa, Mieko,Ichikawa, Takuya,Yamaguchi, Masahiko
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supporting information
p. 4327 - 4329
(2013/07/26)
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- Regioselective C-S bond formation accomplished by regioselective C-F substitution of polyfluoroarenes with substituted thiophenols
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The nucleophilic aromatic substitution reaction of pentafluorobenzene, methyl 2,3,4,5-tetrafluorobenzoic acid ester and 1,2,4,5-tetrafluorobenzene with substituted thiophenols showed good regioselectivity while pentafluorobenzene gave high yields. The com
- Zhou, Qizhong,Zhang, Bin,Gu, Haining,Zhong, Aiguo,Du, Tieqi,Zhou, Qiong,Ye, Yuyuan,Jin, Zhengneng,Jiang, Huajiang,Chen, Rener
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experimental part
p. 175 - 182
(2012/07/14)
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- THE THIOLATE ANION AS A NUCLEOPHILE. PART XIII. REACTIONS OF SOME TIN(II) AROMATIC THIOLATES
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The reactions of tin(II) benzenethiolate and p-toluenethiolate with various fluoroaromatics in DMF have been studied.Replacement of some of the aromatic fluorines by the thiolate group was observed.The tin(II) aromatic thiolates are comparable in reactivity in these reactions with lead(II) benzenethiolate.All new compound have been characterized by elemental analysis, and NMR (H-1 and F-19) and mass spectroscopy.
- Hynes, Rosemary C.,Peach, Michael E.
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p. 129 - 134
(2007/10/02)
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- REACTIONS OF SOME BROMOFLUOROBENZENES WITH COPPER(I) BENZENETHIOLATE
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The reactions of copper(I) benzenethiolate with some bromofluorobenzenes have resulted in the replacement of the bromine by a phenylthio group.Combinations of this method and the reactions of sodium thiolates with fluorobenzenes have enabled various isomeric phenylthio substituted fluorobenzenes C6HxFy(SR)z to be prepared.The new products have been characterized by elemental analysis, mass, infrared, and fluorine NMR spectroscopy.
- Peach, Michael E.,Sutherland, David J.
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p. 225 - 232
(2007/10/02)
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