147164-48-5

Upstream product

• 108-22-5 Isopropenyl acetate 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 108-24-7 acetic anhydride 

Downstream Products

• 172585-57-8 (R)-acetic acid 1-(4-fluoro-phenyl)-ethyl ester 
• 41024-58-2 1-(4-fluorophenyl)-2-(phenylsulfonyl)-1-ethanone 
• 82415-38-1 ethyl 1-hydroxy-2-oxo-1-cyclopentanecarboxylate 
• 1339838-72-0 1-(4'-fluorophenyl)-4,4,4-trifluoro-1-butanone 
• 1449549-55-6 benzyl 4-(4-fluorophenyl)-4-oxo-2-phenylbutanoate 
• 756489-25-5 4-(4-fluoro-phenyl)-4-oxo-butyronitrile 

Relevant academic research and scientific papers

Visible-Light-Promoted Synthesis of α-CF2H-Substituted Ketones by Radical Difluoromethylation of Enol Acetates

An efficient and novel visible-light-promoted radical difluoromethylation of enol acetates for the synthesis of α-CF2H-substituted ketones has been described. Upon irradiation under blue LED with catalytic amounts of fac-Ir(ppy)3, this photocatalytic procedure employs difluoromethyltriphenylphosphonium bromide as a radical precursor. Various α-CF2H-substituted ketones are successfully created via designed systems based on the SET process. The methodology has also provided an operationally simple process with broad functional group compatibility.

Synthesis of 1,4-Dicarbonyl Compounds by Visible-Light-Mediated Cross-Coupling Reactions of α-Chlorocarbonyls and Enol Acetates

Herein, we report a protocol for visible-light-mediated radical coupling reactions of α-chloroketones and enol acetates to afford 1,4-dicarbonyl compounds, which are important precursors and intermediates in organic synthesis. The reaction involves photoredox-catalyzed activation of the α-chloroketone upon photoelectron transfer, carbon–chlorine bond cleavage, and coupling of the resulting radical with the carbon–carbon double bond of the enol acetate. This mild protocol has a wide substrate scope and moderate to good yields. (Figure presented.).

Visible light induced C-H monofluoroalkylation to synthesize 1,4-unsaturated compound

We developed a method to synthesize fluorinated 1,4-unsaturated dicarbonyl compounds via photoredox catalyzed radical addition process. Commercially available ethyl bromodifluoroacetate (BrCF2CO2Et) as fluoroalkyl source, the corresponding fluoro-containing dicarbonyl compounds could be obtained in moderate to good yields.

Reductive Coupling between C-N and C-O Electrophiles

The cross-electrophile reaction is a promising strategy for C-C bond formation. Recent studies have focused mainly on reactions with organic halides. Here we report a coupling reaction between C-N and C-O electrophiles that demonstrates the possibility of constructing a C-C bond via C-N and C-O cleavage. Several reactions between benzyl/aryl ammonium salts and vinyl/aryl C-O electrophiles have been studied. Preliminary mechanistic studies revealed that the benzyl ammoniums were activated through a radical mechanism.

Ag2CO3-mediated direct functionalization of alkyl nitriles: Facile synthesis of γ-ketonitriles through nitrile alkylation of enol acetates

Direct C(sp3)-H functionalization of alkyl nitriles is a low toxic and facile route to nitrile-containing compounds. In this research, the Ag2CO3-mediated nitrile methylenation of enol acetates is developed to prepare γ-ketonitriles through the direct C(sp3)-H oxidative functionalization of acetonitrile. A radical pathway is proposed, and acetonitrile serves both as solvent and CN-containing radical source.

Formation of δ-Lactones with anti-Baeyer–Villiger Regiochemistry: Investigations into the Mechanism of the Cerium-Catalyzed Aerobic Coupling of β-Oxoesters with Enol Acetates

The cerium-catalyzed, aerobic coupling of β-oxoesters with enol acetates and dioxygen yields δ-lactones with a 1,4-diketone moiety. In contrast to the Baeyer–Villiger oxidation (BVO), where the higher substituted residue migrates; in the case of this oxid

Iron-Catalyzed Cross-Coupling of Alkenyl Acetates

Stable C-O linkages are generally unreactive in cross-coupling reactions which mostly employ more electrophilic halides or activated esters (triflates, tosylates). Acetates are cheap and easily accessible electrophiles but have not been used in cross-couplings because the strong C-O bond and high propensity to engage in unwanted acetylation and deprotonation. Reported herein is a selective iron-catalyzed cross-coupling of diverse alkenyl acetates, and it operates under mild reaction conditions (0 C, 2 h) with a ligand-free catalyst (1-2 mol%). Iron clad: Acetates are underutilized electrophiles in metal-catalyzed cross-coupling reactions because of the strong alkenyl C-O bond and their propensity to engage in unwanted reactions. Combination of a ligand-free low-valent Fe catalyst with nucleophilic organomagnesium reagents, low temperature, and short reaction times results in highly selective cross-couplings with alkenyl acetates.

Homolytic carbostannylation of alkenes and alkynes with tributylstannyl enolates

matrix presented In the presence of AIBN, tributylstannyl enolates derived from aromatic ketones reacted with electron-deficient alkenes and a variety of alkynes to give the corresponding carbostannylated adducts. The reactions with methyl acrylate gave α-tributylstannylmethyl-γ-ketoesters, unlike the known Michael-type reaction of stannyl enolates forming δ-ketoesters. The carbostannylation of alkynes proceeded in an anti addition mode to afford β,γ-unsaturated ketones. The reactivity of stannyl enolates as radical transfer agents could be utilized for radical cyclization of 1,6-enynes.