643-77-6

Upstream product

• 2882-19-1 ethyl 2-phenyl-2-bromoacetate 
• 78935-61-2 (Z)-((1-ethoxy-2-phenylvinyl)oxy)trimethylsilane 
• 28744-77-6 sodium diethyl-2-phenylmalonate 
• 101-97-3 Ethyl 2-phenylethanoate 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 1117-96-0 Diazoethan 
• 1578-63-8 d'acide 2-fluoro-2-phenyl acetique 
• 19242-50-3 ethyl 3-hydroxy-2-phenylprop-2-enoate 
• 4870-65-9 2-bromophenylacetic acid 
• 37167-62-7 bromo-phenyl-acetic acid methyl ester 
• 1006904-71-7 2-(dimethylamino)-1,3-dimethylimidazolidin-2-ylium trifluoromethanolate 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 178552-83-5 C₁₁H₁₁F₃O₅S 
• 401-55-8 ethyl bromofluoroacetate 

Downstream Products

• 21120-42-3 6-phenyl-decan-5-one 
• 32154-48-6 4-Fluoro-2,2-dimethyl-3-oxo-4-phenyl-butyric acid ethyl ester 
• 29114-82-7 1-Fluoro-1-phenyl-hexan-2-one 
• 21120-43-4 1-phenyl-1-fluoro-2-propanone 
• 3468-99-3 ethyl diphenylacetate 
• 1578-63-8 d'acide 2-fluoro-2-phenyl acetique 
• 2802-98-4 diethyl 2-fluoro-2-phenylmalonate 
• 13344-76-8 α-fluorobenzeneacetaldehyde 
• 1578-78-5 α-fluoro-α-phenylmalonic acid 
• 63818-94-0 (R)-α-fluoro-α-phenylacetic acid 
• 63818-95-1 S(+)-acide fluoro-2 phenyl-2 acetique 
• 14204-09-2 N_.N-Dimethyl-2-fluor-2-phenyl-aethylamin 
• 14204-07-0 2-fluoro-2-phenylacetamide 
• 14204-06-9 α-fluoro-N,N-dimethylbenzeneacetamide 

Relevant academic research and scientific papers

Divergent Synthesis of α-Fluorinated Carbonyl and Carboxyl Derivatives by Double Electrophilic Activation of Amides

A straightforward and divergent entry to α-fluorinated carbonyl and carboxyl derivatives is reported. Upon activation of amides with triflic anhydride and a 2-halo-pyridine and subsequent trapping of the resulting keteniminium ions with nucleophiles followed by a second electrophilic activation with NFSI and final hydrolysis, a range of amides can be transformed to α-fluorinated ketones, esters, and amides under mild conditions. Moreover, this reaction can be performed to yield enantioenriched products with a traceless chiral auxiliary.

Nickel-Catalyzed Cross-Coupling of Ethyl Chlorofluoroacetate with Aryl Bromides

A combinatorial nickel-catalyzed monofluoroalkylation of aryl bromides with the industrial raw regent ethyl chlorofluoroacetate has been developed. The two key factors to successful conversion are the combination of nickel with readily available nitrogen and phosphine ligands and the using of a mixture of different solvents. Mechanistic investigations indicated a new zinc regent might generated in situ and be involved in the reaction process.

Organo-catalyzed Michael addition of 2-fluoro-2-arylacetonitriles

An efficient synthesis of a variety of 2-arylacetonitriles containing a fluorinated stereogenic center through organo-catalyzed Michael addition reaction of 2-fluoro-2-arylacetonitriles has been developed. This protocol uses a cheap organocatalyst (DBU) and has a broad substrate scope: α, β-unsaturated ketones, esters, nitriles and sulfones were all successfully reacted. Importantly, water proved to be a good solvent for this reaction.

AZABICYCLO AND DIAZEPINE DERIVATIVES FOR TREATING OCULAR DISORDERS

The present invention provides in one aspect azabicycio and diazepine derivatives useful as modulators of muscarinic receptors. In another aspect, the present invention provides pharmaceutical compositions for treating ocular diseases, the compositions comprising at least one muscarinic receptor modulator. Formulae (I) & (II):

Synthesis of 18F-difluoromethylarenes using aryl boronic acids, ethyl bromofluoroacetate and [18F]fluoride

Herein, we report the radiosynthesis of 18F-difluoromethylarenes via the assembly of three components, a boron reagent, ethyl bromofluoroacetate, and cyclotron-produced non-carrier added [18F]fluoride. The two key steps are a copper-catalysed cross-coupling reaction, and a Mn-mediated 18F-fluorodecarboxylation.

Copper-Mediated Synthesis of Monofluoro Aryl Acetates via Decarboxylative Cross-Coupling

We report the Cu-promoted oxidative cross-coupling of α-fluoromalonate half-esters and aryl boron reagents to deliver mono-fluoro α-aryl acetates under mild conditions (in air at room temperature). The reaction uses a simple, readily available monofluorinated building block to generate arylated compounds with functional groups that are not easily tolerated by existing methods, such as aryl bromides, iodides, pyridines, and pyrimidines.

Enantioselective Hydrogen Atom Transfer: Discovery of Catalytic Promiscuity in Flavin-Dependent 'Ene'-Reductases

Flavin has long been known to function as a single electron reductant in biological settings, but this reactivity has rarely been observed with flavoproteins used in organic synthesis. Here we describe the discovery of an enantioselective radical dehalogenation pathway for α-bromoesters using flavin-dependent 'ene'-reductases. Mechanistic experiments support the role of flavin hydroquinone as a single electron reductant, flavin semiquinone as the hydrogen atom source, and the enzyme as the source of chirality.

Decarboxylative fluorination of β-Ketoacids with N-fluorobenzenesulfonimide (NFSI) for the synthesis of α-fluoroketones: Substrate scope and mechanistic investigation

Cesium carbonate (Cs2CO3)-mediated decarboxylative fluorination of β-ketoacids using NFSI in the MeCN/H2O mixed solvent system affords α-fluoroketones with a broad scope. Both electron-rich and electron-deficient α-non-substituted β-ketoacids are amenable to this protocol. The mechanistic study indicates that the reaction proceeds through electrophilic fluorination followed by decarboxylation, which is different from the decarboxylative fluorination of normal carboxylic acids.

Synthesis, Characterization, and Reactivity of Palladium Fluoroenolate Complexes

Cross-coupling reactions of aryl groups with α-fluoro carbonyl compounds catalyzed by palladium complexes have been reported, but palladium fluoroenolate intermediates relevant to such reactions have not been isolated or even detected previously. We report the synthesis, structural characterization, and reactivity of a series of C-bound arylpalladium fluoroenolate complexes ligated by monophosphines and bisphosphines. DPPF-ligated arylpalladium fluoroenolate complexes (DPPF = 1,1-bis(diphenylphosphino)-ferrocene) derived from a monofluoroester, a difluoroester, difluoroamides, and difluoroacetonitrile underwent reductive elimination in high yields. Reductive elimination was faster from complexes containing less electron-withdrawing fluoroenolate groups and longer Pd-C(enolate) bonds than from complexes containing more electron-withdrawing fluoroenolate groups and shorter Pd-C(enolate) bonds. The rates of reductive elimination from these C-bound fluoroenolate complexes were significantly faster than those of the analogous trifluoromethyl complexes.

Combinatorial Nickel-Catalyzed Monofluoroalkylation of Aryl Boronic Acids with Unactivated Fluoroalkyl Iodides

A combinatorial nickel-catalyzed cross-coupling between arylboronic acids and unactived 1-fluoro-1-iodoalkanes has been developed, which demonstrated high efficiency, mild conditions, and excellent functional-group compatibility. Readily available nitrogen and phosphine ligands were combined with a nitrogen source, which in situ generated a variety of easily tunable catalysts to promote the fluoroalkylation for broad scopes of both coupling partners. This new strategy on combinatorial catalysis offers new solutions for nickel-catalyzed cross-coupling reactions.