130754-15-3

Upstream product

• 35553-92-5 ETHYL 3-METHOXYPHENYLACETATE 
• 401-55-8 ethyl bromofluoroacetate 
• 10365-98-7 3-methoxyphenylboronic acid 
• 79421-99-1 tris(3-methoxyphenyl)-1,3,5,2,4,6-trioxatriborinane 
• 100701-49-3 3-ethoxy-2-fluoro-3-oxopropionic acid 
• 2398-37-0 3-methoxyphenyl bromide 
• 401-56-9 ethyl chlorofluoroacetate 
• 766-85-8 3-methoxy-1-iodobenzene 
• 53392-03-3 (3-methoxyphenyl)triethoxysilane 
• 1798-09-0 m-methoxyphenylacetic acid 

Relevant academic research and scientific papers

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.

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.

Palladium-Catalyzed Cross-Coupling of Ethyl Bromodifluoroacetate with Aryl Bromides or Triflates and Cross-Coupling of Ethyl Bromofluoroacetate with Aryl Iodides

A palladium-catalyzed Negishi cross-coupling reaction of ethyl bromodifluoroacetate with aryl bromides or aryl triflates to construct C(sp2)-CF2 bonds is described. The reaction was conducted under mild reaction conditions, and no preparation of organozinc reagents is required. This is the first report encompassing the conversion of aryl triflates into products containing C-CF2 bonds. In addition, the construction of C(sp2)-CHF bonds was achieved under mild conditions via a cross-coupling of aryl iodides with ethyl bromofluoroacetate.

Nickel-Catalyzed Monofluoroalkylation of Arylsilanes via Hiyama Cross-Coupling

The first example of nickel-catalyzed monofluoroalkylation of arylsilanes has been developed with readily available fluoroalkyl halides. This novel transformation has demonstrated high reactivity, broad substrate scope, excellent functional group tolerance, and mild reaction conditions. The selective activation of a relatively inert C-Si bond for slow release of aryl carbanion is the key reason for reducing the amount of arylmetal species, which makes this method more promising for fluorine-containing modification of complex bioactive molecules. Mechanistic investigations indicate that a free fluoroalkyl radical is involved in this catalytic cycle.

Nickel-catalyzed monofluoromethylation of aryl boronic acids

Aryl boronic acids can be monofluoromethylated under nickel catalysis. The utility of this method is demonstrated by the monofluoromethylation of a borylated and acyl-protected derivative of the statin drug ezetimibe. Mechanistic investigations indicate that a fluoromethyl radical is involved in the NiI/NiIII catalytic cycle.

Palladium-catalyzed cross-coupling of ethyl α-bromo-α- fluoroacetate with arylboronic acids: Facile synthesis of α-aryl-α- fluoroacetate

Palladium-catalyzed Suzuki-Miyaura coupling reactions of ethyl α-bromo-α-fluoroacetate with various structurally diverse arylboronic acids using a phosphine ligand proceeded smoothly to afford α-aryl-α-fluoroacetate in moderate to good yields. This method provides a practical and efficient route to diverse α-monofluorinated α-arylcarbonyl compounds. Georg Thieme Verlag Stuttgart New York.

ELECTRFLUORATION EN POSITION BENZYLIQUE DANS LE SULFOLANE

The use of sulfolane as a solvent instead of acetonitrile in the electrofluorination of benzylic derivatives 1, (R=H, Cl) gives greater yields of benzylic fluorides 2, since the formation of acetamide byproducts 4 is prevented.However, the parallel fluorination of the aromatic nucleus is not avoided under these conditions.