610-60-6Relevant academic research and scientific papers
Copper-catalyzed chemoselective oxidative o-aroylation of 2-acetylphenols, alkyl salicylates and 1,3-dicarbonyl compounds using styrene derivatives
Kumar, Upendra,Sharma, Ajay,Kumar, Naveen,Pandey, Satyendra Kumar
, (2021/03/03)
A novel copper-catalyzed chemoselective oxidative O-aroylation of 2-acetylphenols, alkyl salicylates and 1,3-dicarbonyl compounds with a wide range of styrene derivatives are described. This approach provides an efficient chemoselective preparation of phenol, alkyl salicylate and enol esters in good to excellent yields. This method represents an alternative protocol for the classical esterification reactions.
Ruthenium(II) Catalysis/Noncovalent Interaction Synergy for Cross-Dehydrogenative Coupling of Arene Carboxylic Acids
Dana, Suman,Chowdhury, Deepan,Mandal, Anup,Chipem, Francis A. S.,Baidya, Mahiuddin
, p. 10173 - 10179 (2018/11/21)
A ruthenium-catalyzed cross-dehydrogenative coupling is developed with the aid of a weakly coordinating carboxylic acid group toward the dimerization of arene carboxylic acids. The protocol is operationally simple and suitable to fabricate diverse homodimerized as well as cross-dimerized products in high yields. Computational insights have also been unveiled to comprehend the plausible reaction mechanism. The critical innovation of the synthetic strategy hinges on the soluble basic additive DBU, which constitutes a synergy of Ru(II)-catalysis with noncovalent interaction and, thus, stabilizes pivotal intermediates to promote the challenging dimerization process.
Chemoselective generation of acyl phosphates, acylium ion equivalents, from carboxylic acids and an organophosphate ester in the presence of a Br?nsted acid
Sumita, Akinari,Otani, Yuko,Ohwada, Tomohiko
supporting information, p. 1482 - 1485 (2017/02/05)
We describe the chemoselective conversion of carboxylic acids to functional aromatic ketones promoted by a tailored organophosphate ester in the presence of a Br?nsted acid. The protonated phosphate ester reacts with the carboxylic acid to form acyl phosphate, which reacts with benzenes to give aromatic ketones, probably through the acylium ion or its equivalent. The reaction time is short even at room temperature, and the reaction is compatible with various other functional groups, including amines, olefins, esters, amides and nitriles.
Submillisecond organic synthesis: Outpacing Fries rearrangement through microfluidic rapid mixing
Kim, Heejin,Min, Kyoung-Ik,Inoue, Keita,Im, Do Jin,Kim, Dong-Pyo,Yoshida, Jun-Ichi
, p. 691 - 694 (2016/05/19)
In chemical synthesis, rapid intramolecular rearrangements often foil attempts at site-selective bimolecular functionalization.We developed a microfluidic technique that outpaces the very rapid anionic Fries rearrangement to chemoselectively functionalize iodophenyl carbamates at the ortho position. Central to the technique is a chip microreactor of our design, which can deliver a reaction time in the submillisecond range even at cryogenic temperatures.The microreactorwas applied to the synthesis of afesal, a bioactive molecule exhibiting anthelmintic activity, to demonstrate its potential for practical synthesis and production.
Cu(II)-catalyzed oxidative esterification of 2-carbonyl substituted phenols from the alcohol oxidation level
Sharma, Satyasheel,Park, Jihye,Kim, Mirim,Kwak, Jong Hwan,Jung, Young Hoon,Kim, In Su
, p. 9391 - 9397 (2013/10/08)
A copper-catalyzed oxidative esterification of 2-carbonyl substituted phenols from the alcohol oxidation level is described. This protocol represents direct access to a range of 2-carbonylated aryl benzoate derivatives, which are important building blocks in the synthesis of natural and pharmacological compounds.
Bio-inspired flavonol and quinolone dioxygenation by a non-heme iron catalyst modeling the action of flavonol and 3-hydroxy-4(1H)-quinolone 2,4-dioxygenases
Pap, József S.,Matuz, Andrea,Baráth, Gábor,Kripli, Balázs,Giorgi, Michel,Speier, Gábor,Kaizer, József
experimental part, p. 15 - 21 (2012/06/15)
The mononuclear complex, FeIII(O-bs)(salen) (salenH2 = 1,6-bis(2-hydroxyphenyl)-2,5-diaza-hexa-1,5-diene; O-bsH = O-benzoylsalicylic acid) was synthesized as synthetic enzyme-depside complex, and characterized by spectroscopic methods and X-ray crystal analysis. The dioxygenation of flavonol (flaH) and 3-hydroxy-4-quinolone (quinH2) derivatives in the presence of catalytic amounts of FeIII(O-bs)(salen) results in the oxidative cleavage of the heterocyclic ring to give the corresponding O-benzoylsalicylic and anthranilic acid derivatives with concomitant release of carbon monoxide. These reactions can be regarded as biomimetic functional models with relevance to the iron-containing flavonol and the cofactor-independent 3-hydroxy-4(1H)-quinolone 2,4-dioxygenases.
Method for Making Carbonates and Esters
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Page/Page column 8, (2010/06/13)
A method for forming a monomeric carbonate includes the step of combining a monofunctional alcohol or a difunctional diol with an ester-substituted diaryl carbonate to form a reaction mixture. Similarly, a method for forming a monomeric ester includes the step of combining a monofunctional carboxylic acid or ester with an ester-substituted diaryl carbonate to form a reaction mixture. These methods further include the step of allowing the reaction mixtures to react to form a monomeric carbonate or a monomeric ester, respectively.
Effect of ortho substituents on carbonyl carbon 13C NMR chemical shifts in substituted phenyl benzoates
Nummert, Vilve,Piirsalu, Mare,Maeemets, Vahur,Vahur, Signe,Koppel, Ilmar A.
experimental part, p. 1155 - 1165 (2010/07/13)
13C NMR spectra of 37 ortho-, meta-, and para-substituted phenyl benzoates, containing substituents in benzoyl and phenyl moiety, 4 ortho-substituted methyl and 5 ethyl benzoates as well as 9 R-substituted alkyl benzoates have been recorded. The influence of the ortho substituents on the carbonyl carbon 13C NMR chemical shift, δCO, was found to be described by a linear multiple regression equation containing the inductive, σI, resonance, σRo, and steric, EsB, or ν substituent constants. For all the ortho-substituted esters containing substituents in the acyl part as well as the phenyl part, the substituent-induced reverse inductive effect (ρIR > 0), and the negative steric effect (δorthosB were observed. In the case of ortho substituents in the phenyl part, the resonance effect was negligible. Due to inductive effect, the ortho electron-withdrawing substituents showed an upfield shift or shielding of the carbonyl carbon, while the electron-donating substituents had an opposite effect. Because of the sterical consequences, ortho substituents revealed a deshielding effect on the 13C NMR chemical shift of the carbonyl carbon. For all the meta- and para-substituted esters, the reverse substituent-induced inductive and resonance effects (ρIR4NBr and 2.25M Bu4NBr, and the IR frequencies, νCO, for the ortho-, meta-, and para-substituted phenyl benzoates and alkyl benzoates were correlated nicely with the corresponding 13C NMR substituent chemical shifts, ΔδCO. Copyright
2-carbomethoxy-3-aryl-8-bicyclo[3.2.1]octanes: Potent non-nitrogen inhibitors of monoamine transporters
Meltzer,Blundell,Yong,Chen,George,Gonzalez,Madras
, p. 2982 - 2991 (2007/10/03)
Cocaine is a potent central nervous system stimulant with severe addiction liability. Its reinforcing and stimulant properties derive from inhibition of monoamine transport systems, in particular the dopamine transporter (DAT). This inhibition results in
Kinetics and mechanism of the oxygenation of potassium flavonolate. Evidence for an electron transfer mechanism
Barhacs, Laszlo,Kaizer, Jozsef,Speier, Gabor
, p. 3449 - 3452 (2007/10/03)
The oxygenation of the potassium salt of flavonol (flaH) in absolute DMF leads to potassium O-benzoylsalicylate and carbon monoxide in 95% yield at 40 °C. Kinetic measurements resulted in the rate law -d[flaK]/dt = k2[flaK][O2]. The rate constant, activation enthalpy, and entropy at 313.16 K are as follows: k2/M-1 s-1 = (3.28 ± 0.10) × 10-1 ΔH?/kJ mol-1 = 29 ± 2, ΔS?/J mol-1 K-1 = -161 ± 6. The reaction fits a Hammett linear free energy relationship for 4′-substituted flavonols, and electron-releasing groups make the oxygenation reaction faster. The anodic oxidation wave potentials Ea of the 4′-substituted flavonolates correlate well with reaction rates. At more negative Ea values faster reaction rates were observed. EPR spectrum of the reaction mixture (g = 2.0038, dH = 1.8 G, aH = 0.9 G) showed the presence of flavonoxyl radical as a result of a SET from the flavonolate to dioxygen.
