129264-94-4Relevant academic research and scientific papers
Copper-Catalyzed Insertion into Heteroatom-Hydrogen Bonds with Trifluorodiazoalkanes
Hyde, Stephen,Veliks, Janis,Liégault, Beno?t,Grassi, David,Taillefer, Marc,Gouverneur, Véronique
, p. 3785 - 3789 (2016)
Copper-catalyzed Si-H, B-H, P-H, S-H, and N-H insertion reactions of 2,2,2-trifluoro-1-diazoethane and 1-aryl 2,2,2-trifluorodiazoethanes generated a large number of new fluorine-containing chemical entities for medicinal chemists. With selected Si-H and
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.).
New sulfuryl fluoride-derived alkylating reagents for the 1,1-dihydrofluoroalkylation of thiols
Foth, Paul J.,Gu, Frances,Bolduc, Trevor G.,Kanani, Sahil S.,Sammis, Glenn M.
, p. 10331 - 10335 (2019/11/20)
Herein, we report a new method for the one-pot synthesis of 1,1-dihydrofluoroalkyl sulfides by bubbling sulfuryl fluoride (SO2F2) through a solution of the corresponding alcohol and thiol. The reaction proceeds through a new class of bis(1,1-dihydrofluoroalkyl) sulfate reagents, to afford the desired 1,1-dihydrofluoroalkyl sulfides in 55-90% isolated yields. The bis(1,1-dihydrofluoroalkyl) sulfates are highly chemoselective for thiol alkylation, and are unreactive with competing, unprotected nucleophiles, including amines, alcohols, and carboxylic acids.
Method for carrying out catalytic synthesis on arene 2,2,2-trifluoro-ethyl sulfide through copper
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Paragraph 0020, (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.
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.
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-
Electrolytic Reactions of Fluoro Organic Compounds. 7. Anodic Methoxylation and Acetoxylation of 2,2,2-Trifluoroethyl Sulfides. Preparation of Highly Useful Trifluoromethylated Building Blocks
Fuchigami, Toshio,Yamamoto, Kayoko,Nakagawa, Yuki
, p. 137 - 142 (2007/10/02)
Anodic methoxylation and acetoxylation of 2,2,2-trifluoroethyl sulfides and the corresponding nonfluorinated sulfides were comparatively studied.It was found that a trifluoromethyl group remarkably promoted anodic substitution and methoxy and acetoxy groups were introduced adjacent to the trifluoromethyl group of the sulfides.Longer perfluoroalkyl groups also promoted these anodic substitutions.These products were shown to be highly useful building blocks fro the synthesis of fluoro organic compounds.
Electrolytic reactions of fluoro organic compounds. 8. Further study on anodic methoxylation and acetoxylation of aryl fluoroalkyl sulfides
Fuchigami, Toshio,Yamamoto, Kayoko,Konno, Akinori
, p. 625 - 634 (2007/10/02)
Anodic α-methoxylation and α-acetoxylation of substituted phenyl 2,2.2-trifluoroethyl sulfides and various fluoroalkyl phenyl sulfides were studied from both synthetic and mechanistic aspects. These anodic reactions were greatly affected by both substituent groups at the benzene ring and fluoroalkyl groups. Electron-donating substituents interfered with the reactions significantly. Strong electron-withdrawing perfluoroalkyl groups(CnFn+1: N = 1-3) remarkably promoted these anodic substitutions while difluoro- and monofluoromethyl groups showed much less substitution.
