82208-42-2

Usage

InChI:InChI=1/C9H5F5O/c10-5-4(2-1-3-15)6(11)8(13)9(14)7(5)12/h3H,1-2H2

Upstream product

• 653-34-9 2,3,4,5,6-pentafluorostyrene 
• 201230-82-2 carbon monoxide 
• 653-37-2 perfluorobenzaldehyde 
• 15269-19-9 2,3,4,5,6-pentafluorocinnamaldehyde 
• 2002-92-8 3-(2,3,4,5,6-pentafluorophenyl)propanoic acid 
• 20461-86-3 2,2-diethoxy acetic acid 
• 2828-18-4 ethyl 3-(pentafluorophenyl)propanoate 

Downstream Products

• 878662-39-6 7-(pentafluorophenyl)-1-hepten-5-ol 

Relevant academic research and scientific papers

Perfluorophenyl phosphonate analogues of aromatic amino acids: Synthesis, X-ray and DFT studies

Novel perfluorophenyl phosphonate analogues of phenylglycine and homophenylalanine were prepared in good to excellent yields, and subjected to solid state characterization by single-crystal X-ray diffraction analysis, and to investigations with the use of

Chemo- and Regioselective Organo-Photoredox Catalyzed Hydroformylation of Styrenes via a Radical Pathway

An unprecedented, chemo- and regioselective, organo-photoredox catalyzed hydroformylation reaction of aryl olefins with diethoxyacetic acid as the formylation reagent is described. In contrast to traditional transition metal promoted ionic hydroformylation reactions, the new process follows a unique photoredox promoted, free radical pathway. In this process, a formyl radical equivalent, produced from diethoxacetic acid through a dye (4CzIPN) photocatalyzed, sequential oxidation-decarboxylation route, regio- and chemoselectively adds to a styrene substrate. Importantly, under the optimized reaction conditions the benzylic radical formed in this manner is reduced by SET from the anion radical of 4CzIPN to generate a benzylic anion. Finally, protonation produces the hydroformylation product. By using the new protocol, aldehydes can be generated regioselectively in up to 90% yield. A broad array of functional groups is tolerated in the process, which takes place under mild, metal-free conditions.

2,5-Disubstituted tetrahydrofurans as selective serotonin re-uptake inhibitors

Enhancement of 5-hydroxytryptamine (5-HT, serotonin) neurotransmission is a viable means of treating depression. On the basis of this observation, agents that inhibit re-uptake of 5-HT were prepared based on (-)-cocaine and aryltropanes as lead compounds

MODULATORS OF CENTRAL NERVOUS SYSTEM NEUROTRANSMITTERS

Disclosed are agents having pharmacological activity against cellular receptors and intracellular singaling, particularly receptors and sigaling pathways of central nervous system (CNS) neurotransmitters. Also disclosed are related methods and compositions for the treatment or prevention of diseases or disorders using the agents.

Solvent-free asymmetric olefin hydroformylation catalyzed by highly cross-linked polystyrene-supported (R,S)-BINAPHOS-Rh(I) complex

Using an (R,S)-BINAPHOS-Rh(I) catalyst that is covalently anchored to a highly cross-linked polystyrene support, asymmetric hydroformylation of olefins was performed in the absence of organic solvents. The reaction of cis-2-butene, a gaseous substrate, provided (S)-2-methylbutanal with 100% regioselectivity and 82% ee upon treatment with H2 (12 atm) and CO (12 atm) in a batchwise reactor equipped with a fixed bed. The polymer-supported catalyst was applicable to a continuous vapor-flow column reactor, and thus, 3,3,3-trifluoropropene was converted into (S)-2-trifluoromethylpropanal with an iso/normal ratio of 95/5 and 90% ee. Less volatile olefins, such as styrene, vinyl acetate, 1-alkenes, and fluorinated alkenes, were successfully converted into the corresponding isoaldehydes with high ee values, when they were injected through a supercritical CO2-flow column reactor. Successive injection of a series of olefins realized the conversion of an olefin library into an optically active aldehyde library.

Highly enantioselective hydroformylation of olefins catalyzed by rhodium(I) complexes of new chiral phosphine-phosphite ligands

A new chiral phosphine-phosphite ligand, (R)-2-(diphenylphosphino)- 1,1'-binaphthalen-2'-yl (S)-1,1'-binaphthalene-2,2'-diyl phosphite [(R,S)- BINAPHOS, (R,S)-2a], was synthesized. Its Rh(I) complex was prepared, and its structure has been characterized by 1H and 31P NMR spectroscopy. Using Rh(I) complexes of (R,S)-2a and its enantiomer, highly enantioselective hydroformylation of styrene has been performed (94% ee, iso/normal = 88/12). The catalyst system was also effective for a variety of other olefins. Some other phosphine-phosphite ligands bearing 1,1'-binaphthyl and biphenyl backbones, such as (S)-3,3'-dichloro-6-(diphenylphosphino)-2,2',4,4'- tetramethylbiphenyl-6'-yl (R)-1,1'-binaphthalene-2,2'-diyl phosphite [(S,R)- BIPHEMPHOS. (S,R)-5a], (R,R)-2a, (R,S)-2b, (R)-2c, and (R)-5b, were tested for asymmetric hydroformylation. The results indicate that the sense of enantioface selection for the prochiral olefins is mainly determined by the absolute configuration of the phosphine site, for example, the (R)-2- (diphenylphosphino)-1,1'-binaphthalen-2'-yl group in (R,S)-2a. The relative configurations of the two biaryl groups in the phosphine-phosphites play crucial roles in the degree of the enantioselectivities, that is, the (R,S)- isomer generally gives products in high ee's and the (R*,R*)-isomer does in low ee's. Treatment of Rh(acac)[(R,S)-2a] with a 1:1 mixture of carbon monoxide and hydrogen gave a hydridorhodium complex. RhH-(CO)2[(R,S)-2a], as a single species. Trigonal bipyramidal structure is suggested for this complex, in which the hydride and the phosphite moiety are located at the apical positions and the phosphine and the two carbonyls occupy the equatorial positions. The interchange of the phosphine and the phosphite sites with each other through rapid pseudorotations has not been observed in RhH(CO)2[(R,S)-2a]. The structural deviations of the monohydride complexes from an ideal trigonal bipyramid seem to be larger in (R*,R*)-isomers than in the corresponding (R*,S*)-isomers. The existence of only one active species involved in the Rh(1)-(R,S)-2a-catalyzed hydroformylation has been manifested by the plot of ln([R]/[S]) of the hydroformylation product vs the reciprocals of the reaction temperatures. The higher thermodynamic stability of Rh(acac)[(R,S)-2a] than its diastereomer Rh(acac)[(R,R)-2a] is demonstrated in relation to the restricted configuration of (R)-2c to (R,S)- 2c in its complex formation with Rh(1).

HOMOGENEOUS CATALYSIS OF MIXED-METAL SYSTEMS. HIGHLY REGIOSELECTIVE HYDROFORMYLATION-AMIDOCARBONYLATION OF A FLUORO OLEFIN CATALYZED BY Co-Rh MIXED-METAL SYSTEMS. OBSERVATION OF CoRh(CO)7 CATALYSIS.

The hydroformylation-amidocarbonylation of a fluoro olefin, C//6F//5CH equals CH//2, catalyzed by Co//2(CO)//8-rhodium carbonyl systems proceeds with excellent regioselectivity. The process includes a unique Co-Rh mixed-metal complex, CoRh(CO)//7, as an a

Hydroformylation of Fluoro Olefins, RfCH=CH2, Catalyzed by Group VIII Transition-Metal Catalysts. Crucial Factors for Extremely High Regioselectivity

Hydroformylations of fluoro olefins, trifluoroprop-1-ene (TFP), pentafluorobut-1-ene (PFB), heptafluoropent-1-ene (HPFP), heptadecafluorodec-1-ene (HPDFD), vinyl fluoride (VF), pentafluorostyrene (PFS), and allylpentafluorobenzene (4a), promoted by transition-metal catalysts were studied.Remarkable dependency of the regioselectivity of the reaction on the catalyst metal species (Co, Pt, Ru, and Rh) was found in the reactions of TFP and PFS; e.g., n-aldehyde was obtained with >93percent selectivity by a cobalt catalyst whereas iso-aldehyde was obtained with >96percent selectivity by a rhodium catalyst for the reaction of TFP.On the contrary, the reaction of VF gave 2-fluoropropanal (2-FPA) exclusively, regardless of the metal catalyst species.The effects of temperature and carbon monoxide pressure on the regioselectivity were investigated.Possible mechanisms for the uniquely regioselective hydroformylations are discussed on the basis of the results obtained, and a mechanism that involves an initial formation of isoalkyl-metal species followed by isomerization to n-alkyl-metal species and/or followed by carbon monoxide insertion to form isoacyl-metal intermediate was proposed to be the one operating in these reactions.