7464-46-2Relevant articles and documents
Transition-Metal-Free DMAP-Mediated Aromatic Esterification of Amides with Organoboronic Acids
Guo, Jiarui,Liu, Lantao,Wang, Tao,Wang, Yanqing,Xu, Kai,Zhang, Yuheng
supporting information, p. 3274 - 3277 (2021/06/26)
A new, transition-metal-free, effective method for aromatic esterification of amides with organoboronic acids has been developed. A wide range of benzoate derivatives were obtained with yields ranging from moderate to good. The catalytic reaction shows a broad substrate scope and excellent functional group tolerance. Conceptually, DMAP mediates the reaction and is crucial for this transformation.
Rhodium-catalyzed synthesis of esters from aryl iodides and alcohols: use of alcohols with/without the assistance of aldehydes as carbon monoxide and nucleophile sources
Kim, Ju Hyun,Park, Hawon,Chung, Young Keun
, p. 190 - 194 (2017/01/12)
A CO-gas-free rhodium-catalyzed alkoxycarbonylation of aryl iodide with alcohols has been developed. Alcohols, with/without the aid of an aldehyde, were used as a carbon monoxide and nucleophile source. The former synthesis afforded better yields of the alkoxycarbonylated products. Moreover, phenols also afforded phenoxycarbonylation products with high yields.
The heteropolyacid catalyzed phenol method for synthesizing Arylester
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Paragraph 0054; 0055, (2016/11/09)
The invention discloses a synthesis method of phenol by aromatic esterification by using heteropoly acid as a catalyst. The method comprises the following steps: adding fatty acid substituted phenol ester I, substituted benzoic acid II, reaction solvent and heteropoly acid into a reaction vessel provided with a thermometer, a water separator and a stirrer, reacting at 110-170 DEG C for 0.5-10 hours, wherein the reaction progress is monitored by TLC (thin layer chromatography) in the reaction process; and after the reaction is finished, centrifuging the reaction solution, taking the supernate, washing to remove the solvent, and carrying out recrystallization or column chromatography on the crude product to obtain the aromatic ester compound III. By using the heteropoly acid as the catalyst, compared with the traditional esterification reaction, the method disclosed by the invention has the advantages of simple after-treatment, and low pollution and environment friendliness due to use of a small amount of acid. The heteropoly acid is a solid acid, and can be recycled by filtration after the reaction is finished. The aromatic esterification reaction of exchanging ester with phenol is adopted to avoid the side reaction caused by high oxidation tendency of the substituted phenol in the reaction, so that the method is simpler to operate and has higher yield.
Titanium superoxide-a stable recyclable heterogeneous catalyst for oxidative esterification of aldehydes with alkylarenes or alcohols using TBHP as an oxidant
Dey, Soumen,Gadakh, Sunita K.,Sudalai
, p. 10631 - 10640 (2015/11/17)
Titanium superoxide efficiently catalysed the oxidative esterification of aldehydes with alkylarenes or alcohols, under truly heterogeneous conditions, to afford the corresponding benzyl and alkyl esters in excellent yields. Mechanistic studies have established that this "one pot" direct oxidative esterification process proceeds through a radical pathway, proven by a FTIR spectral study of a titanium superoxide-aldehyde complex as well as spin trapping experiments with TEMPO. The intramolecular version of this protocol has been successfully demonstrated in the concise synthesis of 3-butylphthalide, an anti-convulsant drug.
Ruthenium/NHC-catalyzed tandem benzylic oxidation/oxidative esterification of benzylic alcohols with phenols
Zhang, Di,Pan, Changduo
experimental part, p. 41 - 45 (2012/06/18)
An efficient methodology to access benzoate derivatives via tandem benzylic oxidation/oxidative esterification of benzylic alcohols with phenols catalyzed by ruthenium/NHC was developed. This operationally simple one-pot process uses O2 as the clean oxidant, producing esters in good to excellent yields.
Palladium/NHC-catalyzed tandem benzylic oxidation/oxidative esterification of benzylic alcohols with phenols
Luo, Fang,Pan, Changduo,Cheng, Jiang,Chen, Fan
supporting information; experimental part, p. 5878 - 5882 (2011/09/12)
A palladium/NHC-catalyzed tandem benzylic oxidation/oxidative esterification of benzylic alcohols with phenols to access aryl benzoate derivatives is described. The procedure tolerates a series of functional groups, such as methoxy, nitro, cyano, chloro, fluoro and bromo groups. Thus, it represents a practically alternative method to access aryl benzoate derivatives.
Palladium/NHC-catalyzed oxidative esterification of aldehydes with phenols
Zhang, Manli,Zhang, Shouhui,Zhang, Guoying,Chen, Fan,Cheng, Jiang
experimental part, p. 2480 - 2483 (2011/05/16)
A palladium-catalyzed oxidative esterification of aldehydes with phenols is described, using air as the clean oxidant. This reaction tolerates many functional groups, providing esters with yields ranging from moderate to excellent.
Investigation of a general base mechanism for ester hydrolysis in C-C hydrolase enzymes of the α/β-hydrolase superfamily: A novel mechanism for the serine catalytic triad
Li, Jian-Jun,Bugg, Timothy D. H.
, p. 507 - 513 (2008/03/28)
Previous mechanistic and crystallographic studies on two C-C hydrolase enzymes, Escherichia coli MhpC and Burkholderia xenovorans BphD, support a general base mechanism for C-C hydrolytic cleavage, rather than the nucleophilic mechanism expected for a ser
Synthesis of novel nitro-substituted triaryl pyrazole derivatives as potential estrogen receptor ligands
Naoum, Fotini,Kasiotis, Konstantinos M.,Magiatis, Prokopios,Haroutounian, Serkos A.
, p. 1259 - 1273 (2008/02/08)
Novel tetrasubstituted pyrazole derivatives bearing a nitro substituent on their A-phenol ring were synthesized and their binding affinity towards the estrogen receptor (ER) subtypes ERα and ERβ was determined. Among compounds tested, the 2-nitrophenol derivative 5c was found to bind satisfactorily to both estrogen receptor subtypes (RBAα=5.17 and RBAβ=3.27). In general, the introduction of a nitro group into the A ring of these compounds was found to benefit their ERβ binding abilities.
Kinetics of the reaction of 4-nitrophenyl benzoates with 4-chlorophenol in the presence of potassium carbonate in dimethylformamide
Os'kina,Vlasov
, p. 865 - 872 (2007/10/03)
The effect of the substituent in the benzoyl group on the relative rate and activation parameters of transesterification of substituted 4-nitrophenyl benzoates with 4-chlorophenol in dimethylformamide in the presence of potassium carbonate was studied by the competing reaction technique. The whole series of benzoates showed the enthalpy-entropy compensation effect. 4-Nitrophenyl benzoates having electronacceptor substituents give rise to isokinetic relationship with an isokinetic temperature β of 382 K. The mechanism of the transesterification process is discussed. Pleiades Publishing, Inc., 2006.