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Upstream product

• 384-64-5 3,3,3-trifluoro-2-phenylpropene 
• 345-60-8 α-(difluoromethyl)styrene 
• 395-01-7 2,2-difluoro-1-phenylethanone 
• 700-59-4 β,β-difluoro-α-methylstyrene 
• 98-86-2 acetophenone 
• 1236300-44-9 1-tert-butyl-1H-tetrazol-5-yl fluoromethyl sulfone 
• 110874-41-4 2-Phenyl-1,1-bis(phenylthio)propane 
• 114263-57-9 C₁₅H₁₅FOS 

Relevant academic research and scientific papers

Stereoselective Synthesis of Terminal Monofluoroalkenes from Trifluoromethylated Alkenes

Herein we report the hydrodefluorination reaction of trifluoromethylated alkenes to access terminal monofluoroalkenes. The use of LiAlH4 allowed the stereoselective synthesis of the terminal monofluoroalkenes in good to excellent yields with good to excel

Catalyzing the Hydrodefluorination of CF3-Substituted Alkenes by PhSiH3. H?Transfer from a Nickel Hydride

The hydrodefluorination of CF3-substituted alkenes can be catalyzed by a nickel(II) hydride bearing a pincer ligand. The catalyst loading can be as low as 1 mol%. gem-Difluoroalkenes containing a number of functional groups can be formed in goo

Selective Copper Complex-Catalyzed Hydrodefluorination of Fluoroalkenes and Allyl Fluorides: A Tale of Two Mechanisms

The transition to more economically friendly small-chain fluorinated groups is leading to a resurgence in the synthesis and reactivity of fluoroalkenes. One versatile method to obtain a variety of commercially relevant hydrofluoroalkenes involves the catalytic hydrodefluorination (HDF) of fluoroalkenes using silanes. In this work it is shown that copper hydride complexes of tertiary phosphorus ligands (L) can be tuned to achieve selective multiple HDF of fluoroalkenes. In one example, HDF of the hexafluoropropene dimer affords a single isomer of heptafluoro-2-methylpentene in which five fluorines have been selectively replaced with hydrogens. DFT computational studies suggest a distinct HDF mechanisms for L2CuH (bidentate or bulky monodentate phosphines) and L3CuH (small cone angle monodentate phosphines) catalysts, allowing for stereocontrol of the HDF of trifluoroethylene.

Photocatalytic alkene reduction by a B12-TiO2 hybrid catalyst coupled with C-F bond cleavage for: Gem -difluoroolefin synthesis

Photocatalytic syntheses of gem-difluoroolefins were performed using the B12-TiO2 hybrid catalyst during the CC bond reduction of α-trifluoromethyl styrenes with C-F bond cleavage at room temperature under nitrogen. The gem-difluoroolefins were used as synthetic precursors for fluorinated cyclopropanes.

1-tert-Butyl-1H-tetrazol-5-yl fluoromethyl sulfone (TBTSO2CH2F): A versatile fluoromethylidene synthon and its use in the synthesis of monofluorinated alkenes via JuliaKocienski olefination

1-tert-Butyl-IH-tetrazol-5-yl fluoromethyl sulfone (TBTSO 2CI-12F) has been developed as a new and efficient fluoromethylidene synthon for the synthesis of both terminal and internal monofluoroalkenes via JuliaKocienski olefination reaction. The base-mediated reaction between TBTSO2CI-12F and carbonyl compounds (aldehydes and ketones) provided terminal monofluoroalkenes in good yields with moderate E!Z selectivity. The dominance of E- or Z-fluoroalkenes could be controlled by selection of proper reaction solvent and temperature. TBTSO 2CI-12F reagent was also found to be readily CL-alkylated, acylated, and phenylsulfonylated to give corresponding CL-functionalized fluorosulfones, which could be used in the synthesis of alkyl-, acyl-, and phenylsulfonyl-substituted internal monofluoroalkenes via JuliaKocienski olefination reactions.

Synthesis of α-fluoro-β-lactones and their thermal conversion to 1-fluoroalkenes

α-Fluoro-β-lactones have been synthesized and isolated for the first time from α-fluoro-β-hydroxy acids by using the couple TsCl/DMAP as lactonization agent. A detailed description of the synthesis and spectroscopic properties of α-fluoro-β-lactones is pr

Synthesis and Horner-Wittig Chemistry of (Fluoromethyl)diphenylphosphane Oxide

(Fluoromethyl)diphenylphosphane oxide (1) was obtained by heating (diphenylphosphinoyl)methyl p-toluenesulfinate (2) with potassium fluoride. Compound 1 is a stable, crystalline solid, suitable for application in the Horner-Wittig reaction. The compound described in the literature under this name was found to be benzylphenylphosphinic fluoride (5). The anion of phosphane oxide 1 readily reacted with a wide range of carbonyl to yield diastereomeric mixtures of α-fluoro-β-(hydroxyalkyl)phosphane oxides (7), which in most cases could be separated. The ease of phosphinate elimination to yield (E)- and (Z)-1-fluoroalkenes 8 stereoselectively was found to be strongly dependent upon conformation and substituent patern. The route presented here avoids the use of hazardous fluorohalomethanes, which were employed in several earlier Wittig-related approaches to vinyl fluorides.

THE PREPARATION OF α-FLUOROSULFOXIDES AND VINYL FLUORIDES

Treatment of thioacetals with HgF2 in anhydrous acetonitrile, followed by oxidation with MCPBA results in the formation of α-fluorosulfoxides, which can be pyrolyzed to give vinyl fluorides.