2262-07-9

Upstream product

• 353-83-3 1,1,1-trifluoro-2-iodoethane 
• 930-69-8 sodium thiophenolate 
• 421-06-7 2-bromo-1,1,1-trifluoroethane 
• 371-67-5 2,2,2-trifluorodiazoethane 
• 108-98-5 thiophenol 
• 931-59-9 benzenesulfenyl chloride 
• 421-04-5 1-chloro-1,1,2-trifluoroethane 
• 75-89-8 2,2,2-trifluoroethanol 
• 591-50-4 iodobenzene 
• 14897-48-4 S-(2,2,2-trifluoroethyl) ethanethioate 
• 5296-64-0 allyl phenyl thioether 
• 373-88-6 2,2,2-trifluroethylamine hydrochloride 
• 5848-60-2 cinnamyl(phenyl)sulfide 
• 5651-88-7 phenyl propargyl sulfide 

Downstream Products

• 56354-44-0 β,β,β-trifluoroethyl phenyl sulfone 
• 26437-91-2 N,N-Diethyl<2-(phenylthio)ethinyl>amin 
• 61698-71-3 Diisopropyl-phenylsulfanylethynyl-amine 
• 108200-49-3 Phenyl 1-methoxy-2,2,2-trifluoroethyl sulfide 
• 108200-50-6 Phenyl 1-acetoxy-2,2,2-trifluoroethyl sulfide 
• 102201-15-0 1,1-dichloro-2,2,2-trifluoroethylthiobenzene 
• 114953-71-8 [(1-chloro-2,2,2-trifluoroethyl)sulfanyl]benzene 
• 79695-52-6 2,2,2-trifluoroethyl phenyl sulfoxide 
• 130612-76-9 (R,S)-1,2,2,2-tetrafluoro-1-(phenylthio)ethane 
• 156082-34-7 (1-Chloro-2,2,2-trifluoro-ethanesulfinyl)-benzene 

Relevant academic research and scientific papers

Synthesis of aryl 2,2,2-trifluoroethyl sulfides

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

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

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.

Synthesis of Sulfonimidamides from Sulfenamides via an Alkoxy-amino-λ6-sulfanenitrile Intermediate

Sulfonimidamides are intriguing new motifs for medicinal and agrochemistry, and provide attractive bioisosteres for sulfonamides. However, there remain few operationally simple methods for their preparation. Here, the synthesis of NH-sulfonimidamides is achieved directly from sulfenamides, themselves readily formed in one step from amines and disulfides. A highly chemoselective and one-pot NH and O transfer is developed, mediated by PhIO in iPrOH, using ammonium carbamate as the NH source, and in the presence of 1 equivalent of acetic acid. A wide range of functional groups are tolerated under the developed reaction conditions, which also enables the functionalization of the antidepressants desipramine and fluoxetine and the preparation of an aza analogue of the drug probenecid. The reaction is shown to proceed via different and concurrent mechanistic pathways, including the formation of novel S≡N sulfanenitrile species as intermediates. Several alkoxy-amino-λ6-sulfanenitriles are prepared with different alcohols, and shown to be alkylating agents to a range of nucleophiles.

Dealkylative intercepted rearrangement reactions of sulfur ylides

Sulfur ylides are well-known to undergo sigmatropic rearrangement reaction. Herein, we describe a novel reactivity of sulfur ylides, which provides access to the product of a formal functional group metathesis upon dealkylative interception of the rearrangement process. Using a simple iron catalyst and in situ generated diazoalkanes this method provides access to α-mercaptoacetonitrile derivatives.

Substituent-dictated partitioning of intermediates on the sulfide singlet oxygen reaction surface. A new mechanism for oxidative C-S bond cleavage in α-hydroperoxy sulfides

The reactions of singlet oxygen with 17 sulfides bearing either anion or radical stabilizing substituents are reported. The abilities of substituents to modify product compositions in both the oxidative cleavage and sulfide oxidation pathways are analyzed in terms of partitioning of the hydroperoxy sulfonium ylide intermediate. Evidence is presented that suggests that the hydroperoxy sulfonium ylide exists in both diradical and zwitterionic forms. In addition, both inter- and intramolecular pathways for decomposition of α-hydroperoxy sulfides are suggested to rationalize the substituent-dependent formation of oxidative C-S bond cleavage products.

Process for preparing trifluoroethyl sulfur compounds from thiolates and 1-chloro-2,2,2-trifluoroethane

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-

Stereochemical study of the allylation of 1-phenylsulfinylethyl and 1- phenylsulfinyl-2,2,2-trifluoroethyl radicals

The stereochemistry of the reactions of 1-phenylsulfinylethyl radical (1r) and 1-phenylsulfinyl-2,2,2-trifluoroethyl radical (2r) with allylstannanes has been examined. Preferential formation of products of opposite relative configuration has been observe

Acid-Catalyzed Reaction of 2,2,2-Trifluorodiazoethane for Analysis of Functional Groups by 19F Nuclear Magnetic Resonance Spectrometry

The acid-catalyzed reactions of trifluorodiazoethane with alcohols, phenols, thiols, and carboxylic acids are reported.The yield data for these trifluoroethyl derivatives suggest a simple, and in many cases, quantitative method for introduction of a fluorine tagging group.The 19F chemical shifts indicate that most functional groups (e.g., phenols, alcohols, etc.) have fairly well resolved chemical shifts regions.In addition, paramagnetic shift reagents have been utilized to selectively differentiate carboxylic acids from other active hydrogen functional groups.

Fluoride Ion Elimination-Addition Reactions. Synthesis of 2,2-Difluoroethenyl Phenyl Selenide and 2,2,2-Trifluoroethyl Phenyl Selenide

2-Chloro-2,2-difluoroethyl phenyl selenide (1) reacts with KF and a catalytic amount of 18-crown-6 to give 2,2-difluoroethenyl phenyl selenide (3) and 2,2,2-trifluoroethyl phenyl selenide (4).The latter is formed by an elimination-addition sequence. 2-Bro