56695-79-5

Upstream product

• 538-44-3 (E)-benzylidenepinacolone 
• 20397-61-9 (Z)-2-fluoro-3-phenylacrylic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 350-90-3 (Z/E)-2-fluoro-3-phenylprop-2-enoic acid 
• 100-52-7 benzaldehyde 
• 101128-06-7 diphenyl-phosphinoxy-fluoroacetate de methyle 
• 1075204-17-9 C₁₁H₇F₇O₄S 
• 32809-84-0 diethyl methyl 1-fluoromethylphosphonocarboxylate 
• 370-07-0 methyl (Z)-2-fluoro-3-phenylpropenoate 
• 108-86-1 bromobenzene 
• 2343-89-7 methyl 2-fluoroprop-2-enoate 
• 591-50-4 iodobenzene 
• 453-18-9 methyl fluoroacetate 
• 117141-34-1 C₉H₇ClF₄O 

Downstream Products

• 115879-17-9 (+)-(R)-3-fluoro-1-<(4-methylphenyl)sulphinyl>-4-phenyl-(3Z)-buten-2-one 
• 20397-61-9 (Z)-2-fluoro-3-phenylacrylic acid 
• 20397-60-8 (E)-2-fluoro-3-phenylprop-2-enoic acid 
• 127146-16-1 (R)-3-fluoro-4-phenyl-1-(p-tolylsulphonyl)but-3-en-2-ol 
• 29900-78-5 MAZ₁₇₀₂ 
• 127146-14-9 (Z)-3-fluoro-4-phenyl-1-(p-tolylsulphonyl)but-3-en-2-one 
• 40235-35-6 methyl 5-phenyl-1H-1,2,3-triazole-4-carboxylate 

Relevant academic research and scientific papers

Fluoro-functionalization mediated by the reactive chalcogen reagents

Two types of fluoro-functionalizations mediated by reactive chalcogen reagents have been summarized. The first is a generation of benzeneselenenyl fluoride and its electrophilic reactions with alkenes, electron-deficient alkenes, isonitriles and α-diazoca

Organocatalyzed Sulfa-Michael Addition of Thiophenols on Trisubstituted α-Fluoroacrylates, a Straightforward Access to Chiral Fluorinated Compounds

In this manuscript, a simple and efficient sulfa-Michael addition reaction of aryl thiols to trisubstituted α-fluoro-α,β-unsaturated esters both in racemic and, for the first time, in enantioselective version is reported. The commercially available dimer of cinchona derivatives (DHQ)2PYR was used as a catalyst. This strategy showed a great tolerance for various substrates and substituents, providing fair to excellent yields, moderate to excellent diastereoselectivities (2:1 to >99:1), and low to good enantioselectivities (2 to 87%). The reaction has been applied to the synthesis of fluorinated analogues of diltiazem and tiazesim, both therapeutic agents.

Stereospecific synthesis of tri- and tetrasubstituted α-fluoroacrylates by mizoroki-heck reaction

Ligand-free, efficient, palladium-catalyzed Mizoroki-Heck reaction between methyl α-fluoroacrylate and arene or hetarene iodides is reported for the first time. The reaction is stereospecific and provides fair to quantitative yields of fluoroalkenes. The Mizoroki-Heck reaction starting from more hindered and usually reluctant trisubstituted acrylate, to access tetrasubstituted fluoroalkenes, is also reported. Finally, the use of a three-step synthesis sequence, including Mizoroki-Heck reaction, allows the synthesis of fluorinated analogues of therapeutic agents with high yield.

A substrate-driven approach to determine reactivities of α,β-unsaturated carboxylic esters towards asymmetric bioreduction

The degree of C=C bond activation in the asymmetric bioreduction of α,β-unsaturated carboxylic esters by ene-reductases was studied, and general recommendations to render these "borderline-substrates" more reactive towards enzymatic reduction are proposed. The concept of "supported substrate activation" was developed. In general, an additional α-halogenated substituent proved to be beneficial for enzymatic activity, whereas β-alkyl or β-aryl substituents were detrimental for the reactivity of nonhalogenated substrates, and α-cyano groups showed little effect. The alcohol moiety of the ester functionality was found to have a strong influence on the reaction rate. Overall, activities were determined by both steric and electronic effects. Biotransformation: The asymmetric bioreduction of α,β-unsaturated carboxylic esters by ene-reductases could be tuned by varying the degree of C=C bond activation (see scheme). An additional α-halogenated substituent proved to be beneficial for enzymatic activity, whereas β-alkyl or β-aryl substituents were detrimental for the reactivity of nonhalogenated substrates. Copyright

Synthetic utilization of 2-chloro-1,1,1,2-tetrafluoroethane

β-Substituted α-fluoro-α,β-unsaturated carboxylic acids have been successfully synthesized, usually in a (Z)-stereospecific manner by way of a stepwise or a one-pot three-step procedure starting from 2-chloro-1,1,1,2-tetrafluoroethane (HCFC-124), one of the major byproducts of the industrial process for tetrafluoroethene formation from chlorofluoromethane (HCFC-22). Get some Z's! β-Substituted α-fluoro-α,β- unsaturated carboxylic acids have been successfully synthesized from 2-chloro-1,1,1,2-tetrafluoroethane, one of the major byproducts of tetrafluoroethene formation from chlorofluoromethane. The products are usually obtained with Z stereoselectivity, by either a stepwise or a one-pot three-step procedure (see scheme).

Highly efficient and stereoselective Julia-Kocienski protocol for the synthesis of α-fluoro-α,β-unsaturated Esters and Weinreb amides employing 3,5-bis(trifluoromethyl)phenyl (BTFP) sulfones

: α-Fluoroacetates 3 and Weinreb amide 4, bearing a α-[3,5-bis(trifluoromethyl)phenyl]sulfonyl (BTFP-sulfonyl) group at the α-position, are employed in the highly stereoselective synthesis of α-fluoro-α,β-unsaturated alkenoates and Weinreb amides, respectively. Aromatic and aliphatic aldehydes are condensed under extremely mild and simple reaction conditions using potassium carbonate in dimethylformamide at room temperature under solid-liquid phase-transfer catalysis conditions in good yields and high Z-diastereoselectivities, specially in the case of the fluorinated Weinreb amides. A detailed computational mechanistic study suggests a final non-concerted elimination of sulfur dioxide and 3,5-bis(trifluoromethyl)phenoxide and explains the observed high stereoselectivities for the reaction on the basis of thermodynamic and kinetic considerations.

Toward (Z)-selective Horner-Wadsworth-Emmons reaction of aldehydes with 2-fluoro-2-diethylphosphonoacetic acid

The stereoselective Horner-Wadsworth-Emmons reaction of aldehydes with 2-fluoro-2-diethylphosphonoacetic acid utilizing i-PrMgBr afforded (Z)-α-fluoro-α,β-unsaturated carboxylic acids as the major products.

tert-Butylsulfinyl-fluoroacetate: Versatile reagent for the preparation of fluoroethylidenoate derivatives

The preparation of (Z)-α-fluoroalkenoates from readily available methyl-tert-butylsulfanyl- or tert-butylsulfinylfluoroacetate 1 or 5 is described. This short synthesis, based on a direct extrusion of SO2 from β-hydroxysulfoxides, presents a mo

Thia-Wittig-like reactions as a new route for the stereoselective synthesis of (Z)-fluoroalkenoates

(matrix presented). Stereoselective syntheses of (Z)-fluoroalkenoates 3a-g have been developed in three steps from the readily available fluorosulfide 5 and aldehydes. This preparation, involving a Durst reaction, was highly stereoselective and led to flu

Chemistry of fluorinated enamines. Novel reaction of trifluoromethylated enamine with Grignard reagents

Trifluoromethylated enamine, N-(2,3,3,3-tetrafluoro-1- propenyl)dimethylamine (1), readily reacted with a variety of Grignard reagents 2 at room temperature to afford the trifluorovinyl compounds 3 in good yields.