441-57-6

Upstream product

• 428-00-2 3-(4-fluoro-phenyl)-3-hydroxy-3-phenyl-propionic acid ethyl ester 
• 352-34-1 4-fluoro-1-iodobenzene 
• 4192-77-2 ethyl cinnamate 
• 462-06-6 fluorobenzene 
• 345-83-5 4-fluorobenzophenone 
• 98-88-4 benzoyl chloride 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 395-21-1 1-(4-fluorophenyl)-1-phenylethylene 
• 109-94-4 formic acid ethyl ester 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 

Downstream Products

• 303110-63-6 (E)-(2S)-2-Ethoxy-3-{4-[3-(4-fluorophenyl)-3-phenyl-allyloxy]-phenyl}-propionic acid ethyl ester 
• 390-42-1 (E/Z)-3-(4-fluorophenyl)-3-phenylpropenoic acid 
• 73244-36-7 1-((E)-3-Bromo-1-phenyl-propenyl)-4-fluoro-benzene 
• 1338381-08-0 3-((4-fluorophenyl)(phenyl)methyl)benzofuran 
• 198889-35-9 C₁₅H₁₃FO 
• 374724-94-4 3-(4-fluorophenyl)-3-phenylpropan-1-ol 
• 1352758-21-4 (E)-3-(4-fluorophenyl)-3-phenylacrylaldehyde 
• 863970-22-3 (S)-3-(4-fluorophenyl)-3-phenylpropanal 
• 198889-39-3 (E)-3-(4-fluorophenyl)-3-phenylprop-2-en-1-ol 

Relevant academic research and scientific papers

Photoinduced Oxidative Alkoxycarbonylation of Alkenes with Alkyl Formates

A photoinduced oxidative alkoxycarbonylation of alkenes initiated by intermolecular addition of alkoxycarbonyl radicals has been demonstrated. Employing alkyl formates as alkoxycarbonyl radical sources, a range of α,β-unsaturated esters were obtained with good regioselectivity and E selectivity under ambient conditions.

Mizoroki–Heck reaction of 1,2-disubstituted aryl alkenes: Variables of synthesis, solvent and ligand modulation of reactivity

Reaction of aryl iodides with 1,2-disubstituted aryl alkenes in the presence of TBABr/TBACl gave high yields of the Mizoroki–Heck product. Phosphine ligands were used for the modulation of reactivity and stereoselectivity, for the reaction of 4-iodoanisole with cinnamaldehyde. tert-Bu3P.HBF4 gave the highest E:Z ratio of 1:0.08. The use of PEG-200 and PEG-400 as solvent could activate the reaction of aryl iodides with various 1,2-disubstituetd aryl alkenes.

Potassium tert-butoxide mediated Heck-type cyclization/isomerization- benzofurans from organocatalytic radical cross-coupling reactions

A transition metal-free Heck-type cyclization/isomerization reaction has been developed. Mediated by potassium tert-butoxide and phenanthroline a variety of benzofuran derivatives have been synthesized.

Arenediazonium salts immobilized in imidazolium ionic liquids as electrophilic partners in the Pd(OAc)2-catalyzed Matsuda-Heck arylation

The utility of arenediazonium salts immobilized in imidazolium-ILs [BMIMPF6 and BMIMBF4] for facile, high yielding, synthesis of olefins via the Pd(OAc)2-catalyzed Matsuda-Heck arylation reaction has been demonstrated. The reaction can also be performed as a two-step process in the IL starting from ArNH2, by sequential in-situ diazotization-arylation. Simple product isolation and the recycling/re-use of the IL are additional advantages of this one-pot method.

Acylguanidines as bioisosteres of guanidines: NG-acylated imidazolylpropylguanidines, a new class of histamine h2 receptor agonists

N1-Aryl(heteroaryl)alkyl-N2-[3-(1H-imidazol-4-yl) propyl]guanidines are potent histamine H2-receptor (H2R) agonists, but their applicability is compromised by the lack of oral bioavailability and CNS penetration. To improve pharmacokinetics, we introduced carbonyl instead of methylene adjacent to the guanidine moiety, decreasing the basicity of the novel H2R agonists by 4-5 orders of magnitude. Some acylguanidines with one phenyl ring were even more potent than their diaryl analogues. As demonstrated by HPLC-MS, the acylguanidines (bioisosteres of the alkylguanidines) were absorbed from the gut of mice and detected in brain. In GTPase assays using recombinant receptors, acylguanidines were more potent at the guinea pig than at the human H2R. At the hH1R and hH3R, the compounds were weak to moderate antagonists or partial agonists. Moreover, potent partial hH4R agonists were identified. Receptor subtype selectivity depends on the imidazolylpropylguanidine moiety (privileged structure), opening an avenue to distinct pharmacological tools including potent H4R agonists.

Mono- and β,β-double-heck reactions of α,β-unsaturated carbonyl compounds in aqueous media

Optimized reaction conditions for the mono- and β,β-diarylation of electron-deficient alkenes in aqueous media catalyzed either by a p-hydroxyacetophenone oxime-derived palladacycle or by palladium(II) acetate under phosphine-free conditions and in the presence of (dicyclohexyl)- methylamine as base are described. Regioselective monoarylation of unsubstituted and substituted α,β-unsaturated carbonyl compounds takes place with aryl iodides at 120 °C in water. Aqueous N,N-dimethylacetamide (DMA), tetra-n-butylammonium bromide (TBAB) as additive, and the palladacycle as catalyst are the most efficient conditions for the coupling with aryl bromides, good stereoselectivities being also obtained in the arylation of crotonates and itaconates, whereas cinnamic derivatives afford lower steroselectivity, with the exception of cinnamic acid and nitrile. β,β-Diarylation of unsubstituted α,β-unsaturated carbonyl compounds can be controlled by using higher loading of the palladacycle and can be performed in refluxing water for aryl iodides, whereas DMA must be used for aryl bromides. Microwave irradiation can be used in the monoarylation of tertbutyl acrylate with aryl iodides in water or the coupling between ethyl cinnamate and aryl bromides in aqueous DMA.