14965-37-8Relevant academic research and scientific papers
Formation of meta-arylsulfanyl- and meta-(alkylsulfanyl)phenols from cyclohexane-1,3-diones
Do Van Thanh, Nhan,Patra, Subrata,Clive, Derrick L.J.
, p. 4343 - 4350 (2018/07/13)
Reaction of cyclohexane-1,3-diones with TsCl/Et3N and treatment of the resulting 3-(tosyloxy)cyclohex-2-en-1-ones with aryl- or alkyl thiols and K2CO3 in MeCN gives 3-(arylsulfanyl)cyclohex-2-en-1-ones or 3-(alkylsulfanyl)cyclohex-2-en-1-ones, respectively. These compounds are easily brominated at C-2 by using NBS in MeCN; exposure to DBU in MeCN at room temperature then causes aromatization to afford meta-arylsulfanyl- and meta-(alkylsulfanyl)phenols.
A mild, one-pot Stadler-Ziegler synthesis of arylsulfides facilitated by photoredox catalysis in batch and continuous-flow
Wang, Xiao,Cuny, Gregory D.,Noel, Timothy
supporting information, p. 7860 - 7864 (2013/08/23)
Visible advance: A mild, one-pot Stadler-Ziegler process for C-S bond formation has been developed. The method employs the photoredox catalyst [Ru(bpy)3Cl2]×6 H2O irradiated with visible light. A variety of aryl-alkyl and diaryl sulfides were prepared from readily available arylamines and aryl/alkylthiols in good yields. The use of a photo microreactor led to a significant improvement with respect to safety and efficiency. Copyright
A general, efficient, and functional-group-tolerant catalyst system for the palladium-catalyzed thioetherification of aryl bromides and iodides
Fernandez-Rodriguez, Manuel A.,Hartwig, John F.
experimental part, p. 1664 - 1672 (2009/07/17)
The cross-coupling reaction of aryl bromides and iodides with aliphatic and aromatic thiols catalyzed by palladium complexes of the bisphosphine ligand CyPF-tBu (1) is reported. Reactions occur in excellent yields, broad scope, high tolerance of functional groups, and with turnover numbers that exceed those of previous catalysts by 2 or 3 orders of magnitude. These couplings of bromo- and iodoarenes are more efficient than the corresponding reactions of chloroarenes and could be conducted with less catalyst loading and/or milder reaction conditions. Consequently, limitations regarding scope and functional group tolerance previously reported in the coupling of aryl chlorides are now overcome.
HIGH-TEMPERATURE ORGANIC SYNTHESIS. XXVIII. LIQUID-PHASE REACTIONS OF THIOLS WITH AROMATIC BROMINE COMPOUNDS
Papernaya, L. K.,Panova, G. M.,Deryagina, E. N.,Voronkov, M. G.
, p. 1774 - 1777 (2007/10/02)
In the liquid phase at 125-215 deg C thiophenol only reacts effectively with 2- and 4-bromophenol, 1-bromo-2-napthol, 1-bromonapthalene, and 9-bromoanthracene, forming the corresponding phenyl aryl sulfides. 2-Thiophenethiol and 1-thionapthol reduce the same bromine derivatives to the corresponding arenes.The disulfides formed here undergo secondary transformations.The reactions of thiophenol with 2- and 4-bromophenol and 1-bromo-2-napthol are convenient preparative methods for the synthesis of the previously difficulty obtainable phenyl hydroxyaryl sulfides.
