62158-92-3Relevant articles and documents
Synthesis of aryl 2,2,2-trifluoroethyl sulfides
Menczinger, Bálint,Nemes, Anikó,Szabó, Dénes,Schlosser, Gitta,Jernei, Tamás,Csámpai, Antal,Rábai, József
, (2020/01/28)
Aryl 2,2,2-trifluoroethyl sulfides were synthesized by copper(I)-catalyzed nucleophilic aromatic substitution reaction (Goldberg-Ullmann coupling). The method requires aryl iodides and 2,2,2-trifluoroethyl thioacetate as starting materials, benzylamine as solvent and base, and copper(I) bromide as a catalyst. The reaction mixture was stirred at 110 °C for 6 h under inert atmosphere to afford the targeted aryl 2,2,2-trifluoroethyl sulfides in moderate to good yield.
Hemin Catalyzed Dealkylative Intercepted [2, 3]-Sigmatropic Rearrangement Reactions of Sulfonium Ylides with 2, 2, 2-Trifluorodiazoethane
Yan, Xiaojing,Li, Chang,Xu, Xiaofei,Zhao, Xiaoyong,Pan, Yuanjiang
, p. 2005 - 2011 (2020/05/18)
A dealkylative intercepted [2, 3]-sigmatropic rearrangement reaction of allylic sulfides with 2, 2, 2-trifluorodiazoethane (CF3CHN2) is reported, the commercially available and biocompatible catalyst hemin was found to efficiently catalyze this transformation across a diverse set of allylic sulfides with in situ generated CF3CHN2, providing excellent yields (up to 99%) under mild condition without inert gas protection. In addition, CF3CHN2 exhibited unique reactivity toward this process compared with other frequently used diazo reagents. This work expands the range of carbene-mediated transformations catalyzed by hemin and introduces a concise and general strategy for exploiting new possibility of reactions concerning organosulfides. (Figure presented.).
Method for carrying out catalytic synthesis on arene 2,2,2-trifluoro-ethyl sulfide through copper
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Paragraph 0021, (2016/10/10)
The invention discloses a method for carrying out catalytic synthesis on arene 2,2,2-trifluoro-ethyl sulfide through copper. The method includes the steps that copper iodide is adopted as a catalyst, diimine is adopted as a bidentate ligand, arene halogen, powdered sulfur and 2,2,2-trifluoro-ethyl iodide are adopted as reactants, sodium borohydride is adopted as a reducing agent, stirring is conducted for 1-24 hours at the temperature of 80 DEG C to 95 DEG C in an N,N-dimethyl formamide solvent, aftertreatment is conducted on reaction liquid after the reaction is completed, and the arene 2,2,2-trifluoro-ethyl sulfide compound is obtained. The synthesis method has the advantages that the catalyst is low in price, easy to obtain and low in toxicity, the raw materials are easy to obtain, operation is easy and convenient, and the universality of functional groups is good.
Copper-Catalyzed 2,2,2-Trifluoroethylthiolation of Aryl Halides
Chen, Shouxiong,Zhang, Mengjia,Liao, Xuebin,Weng, Zhiqiang
, p. 7993 - 8000 (2016/09/09)
Herein, a copper-catalyzed 2,2,2-trifluoroethylthiolation reaction of aryl bromides and iodides with elemental sulfur, and 1,1,1-trifluoro-2-iodoethane is described. The reaction showed excellent functional group tolerance and allowed the synthesis of various substituted aryl 2,2,2-trifluoroethyl thioethers with good to excellent yields. This transformation constitutes a one-pot synthesis of 2,2,2-trifluoroethylthiolated compounds from inexpensive, readily available starting materials. Utility of the protocol was further demonstrated in the late-stage synthesis of the pirfenidone derivative. The copper thiolate species were prepared and proposed as key intermediates in the catalytic cycle.
Photoredox Mediated Nickel Catalyzed Cross-Coupling of Thiols with Aryl and Heteroaryl Iodides via Thiyl Radicals
Oderinde, Martins S.,Frenette, Mathieu,Robbins, Daniel W.,Aquila, Brian,Johannes, Jeffrey W.
supporting information, p. 1760 - 1763 (2016/03/01)
Ni-catalyzed cross-couplings of aryl, benzyl, and alkyl thiols with aryl and heteroaryl iodides were accomplished in the presence of an Ir-photoredox catalyst. Highly chemoselective C-S cross-coupling was achieved versus competitive C-O and C-N cross-couplings. This C-S cross-coupling method exhibits remarkable functional group tolerance, and the reactions can be carried out in the presence of molecular oxygen. Mechanistic investigations indicated that the reaction proceeded through transient Ni(I)-species and thiyl radicals. Distinct from nickel-catalyzed cross-coupling reactions involving carbon-centered radicals, control experiments and spectroscopic studies suggest that this C-S cross-coupling reaction does not involve a Ni(0)-species.
Insight into "entrainment" in SRN1 reactions of 2,2-dichloro-1,1,1-trifluoroethane(HCFC-123) with thiolates initiated by Na2S2O4
Tang, Xiao-Jun,Chen, Qing-Yun
, p. 1 - 5 (2015/03/05)
An interesting entrainment process in SRN1 reactions of 2,2-dichloro-1,1,1-trifluoroethane (HCFC-123) with thiolates were studied by experiments and DFT calculations. The radical-anion intermediate, generated from coupling of the fluorinated ra
Copper-mediated radical cross-coupling reaction of 2,2-dichloro-1,1,1- trifluoroethane (HCFC-123) with phenols or thiophenols
Tang, Xiao-Jun,Chen, Qing-Yun
supporting information, p. 6214 - 6217 (2013/02/22)
A copper-mediated cross-coupling reaction between HCFC-123 and phenols or thiophenols has been achieved. It is found that diethyl amine, which serves as both the activator and ligand of copper, plays a key role in this reaction. Two possible radical involved processes are proposed for the reaction mechanism.
Synthesis of new synthons for organofluorine compounds from Halothane containing sulfur functional groups
Kato, Makoto,Maeda, Kensuke,Sato, Kazuyuki,Omote, Masaaki,Ando, Akira,Kumadaki, Itsumaro
, p. 683 - 686 (2007/10/03)
To develop new synthons for the syntheses of organofluorine compounds, the treatment of Halothane, 2-bromo-2-chloro-1,1,1-trifluoroethane, (1) with 4-methylbenzenethiol (2) in the presence of sodium hydride gave 1-chloro- 2,2,2-trifluoroethyl 4-methylphenyl sulfide (3), which was oxidized with m- chloroperbenzoic acid (m-CPBA) to the corresponding sulfoxide (4) and sulfone (5). Reaction of 3 and 5 with allyltributyltin in the presence of 2,2'- azobis(isobutyronitrile) (AIBN) gave 1-(trifluoromethyl)-3-butenyl compounds (9, 11). Sulfoxide 4 was decomposed in this condition. The treatment of 3 with allyltrimethylsilane in the presence of Lewis acids gave 1- (trifluoromethyl)-3-butenyl compounds (9) in good yield. This result suggests that 4-methylphenylthio substituent stabilizes the α-carbocation effectively, though the trifluoromethyl group destabilizes it strongly. Aromatic compounds similarly reacted with 3 in the presence of titanium(IV) chloride to give 2-aryl-1,1,1-trifluoro-2-(4-methylphenylthio)ethanes. Thus, sulfur compounds derived from Halothane were found to be useful new synthons for organofluorine compounds.
Process for preparing trifluoroethyl sulfur compounds from thiolates and 1-chloro-2,2,2-trifluoroethane
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, (2008/06/13)
Process for preparing trifluoroethyl sulfur compounds from thiolates and 1-chloro-2,2,2-trifluoroethane. The invention relates to the preparation of trifluoroethyl sulfur compounds of the formula RSCH2 CF3 by reacting 1-chloro-2,2,2-
