611-95-0Relevant academic research and scientific papers
Light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C-H bonds
Fu, Hua,Liu, Can,Liu, Yong,Yang, Haijun,Zhu, Xianjin
supporting information, p. 4357 - 4363 (2020/07/14)
Visible light-induced organic reactions are important chemical transformations in organic chemistry, and their efficiency highly depends on suitable photocatalysts. However, the commonly used photocatalysts are precious transition-metal complexes and elaborate organic dyes, which hamper large-scale production due to high cost. Here, for the first time, we report a novel strategy: light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C-H bonds, allowing high-value-added aromatic ketones and carboxylic acids to be easily prepared in high-to-excellent yields using readily available alkyl arenes, methyl arenes and aldehydes as materials. The mechanistic investigations showed that the treatment of inexpensive and readily available sodium trifluoromethanesulfinate with oxygen under irradiation of light could in situ form a pentacoordinate sulfide intermediate as an efficient photosensitizer. The method represents a highly efficient, economical and environmentally friendly strategy, and the light and oxygen-enabled sodium trifluoromethanesulfinate photocatalytic system represents a breakthrough in photochemistry. This journal is
Photoinduced Carbon Tetrabromide Initiated Aerobic Oxidation of Substituted Toluenes to Carboxylic Acids
Li, Xiaoqing,Xu, Xiangsheng,Yan, Xiaoyu,Yan, Xinhuan,Zhang, Guofu,Zheng, Kun
, p. 272 - 274 (2020/02/18)
A mild and metal-free procedure is reported for the aerobic oxidation of substituted toluenes to carboxylic acids by using CBr 4 as initiator under irradiation from a 400 nm blue light-emitting diode.
A Bifunctional Iron Nanocomposite Catalyst for Efficient Oxidation of Alkenes to Ketones and 1,2-Diketones
Ma, Zhiming,Ren, Peng,Song, Tao,Xiao, Jianliang,Yang, Yong,Yuan, Youzhu
, p. 4617 - 4629 (2020/05/19)
We herein report the fabrication of a bifunctional iron nanocomposite catalyst, in which two catalytically active sites of Fe-Nx and Fe phosphate, as oxidation and Lewis acid sites, were simultaneously integrated into a hierarchical N,P-dual doped porous carbon. As a bifunctional catalyst, it exhibited high efficiency for direct oxidative cleavage of alkenes into ketones or their oxidation into 1,2-diketones with a broad substrate scope and high functional group tolerance using TBHP as the oxidant in water under mild reaction conditions. Furthermore, it could be easily recovered for successive recycling without appreciable loss of activity. Mechanistic studies disclose that the direct oxidation of alkenes proceeds via the formation of an epoxide as intermediate followed by either acid-catalyzed Meinwald rearrangement to give ketones with one carbon shorter or nucleophilic ring-opening to generate 1,2-diketones in a cascade manner. This study not only opens up a fancy pathway in the rational design of Fe-N-C catalysts but also offers a simple and efficient method for accessing industrially important ketones and 1,2-diketones from alkenes in a cost-effective and environmentally benign fashion.
A Sunscreen-Based Photocage for Carbonyl Groups
Lineros-Rosa, Mauricio,Miranda, Miguel A.,Lhiaubet-Vallet, Virginie
, p. 7205 - 7211 (2020/05/08)
Photolabile protecting groups (PPGs) have been exploited in a wide range of chemical and biological applications, due to their ability to provide spatial and temporal control over light-triggered activation. In this work, we explore the concept of a new photocage compound based on the commercial UVA/UVB filter oxybenzone (OB; 2-hydroxy-4-methoxybenzophenone) for photoprotection and controlled release of carbonyl groups. The point here is that oxybenzone not only acts as a mere PPG, but also provides, once released, UV photoprotection to the carbonyl derivative. This design points to a possible therapeutic approach to reduce the severe photoadverse effects of drugs containing a carbonyl chromophore.
Synthesis method of benzoic acid compounds
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Paragraph 0174; 0175; 0176; 0177, (2019/12/25)
The invention discloses a photocatalytic oxidation synthesis method of benzoic acid compounds, and the photocatalytic oxidation synthesis method comprises the following specific steps: mixing and dissolving toluene compounds and a catalyst in a solvent, reacting for 24-60h in the presence of an oxidant under the conditions of 350-460 nm LED illumination and a temperature of 20-80 DEG C, and performing post-treatment on the reaction liquid to obtain the benzoic acid compounds. The photocatalytic oxidation synthesis method has the advantages of no need of metal catalysts, simple operation and mild reaction conditions; oxygen is used as an oxidant, and the photocatalytic oxidation synthesis method has high atom economy, cheap reagent and environmental protection. The photocatalytic oxidationsynthesis method has good substrate applicability, and various substituents can realize the synthesis of corresponding benzoic acid compounds.
Transition-metal-free carbonylation of aryl halides with arylboronic acids by utilizing stoichiometric CHCl3 as the carbon monoxide-precursor
Xu, Fangning,Li, Dan,Han, Wei
supporting information, p. 2911 - 2915 (2019/06/18)
Under transition-metal-free conditions, carbonylative Suzuki couplings of aryl halides with arylboronic acid using stoichiometric CHCl3 as the carbonyl source has been developed. The simple, efficient, and environmentally benign method was successfully applied to the synthesis of Fenofibric acid, naphthyl phenstatin, and carbon-13 labeled biaryl ketone.
Transition-Metal-Free Carbonylative Suzuki-Miyaura Reactions of Aryl Iodides with Arylboronic Acids Using N-Formylsaccharin as CO Surrogate
Yu, Dezhong,Xu, Fangning,Li, Dan,Han, Wei
supporting information, p. 3102 - 3107 (2019/05/21)
Unprecedented, high yielding, transition-metal-free carbonylative Suzuki-Miyaura reactions of aryl iodides with arylboronic acids using N-formylsaccharin as CO surrogate have been developed. Notably, this general protocol was adapted to the synthesis of the triglyceride and cholesterol regulator drug, fenofibrate, and carbon-13 labeled biaryl ketone. (Figure presented.).
Design and synthesis of new benzophenone derivatives with in vivo anti-inflammatory activity through dual inhibition of edema and neutrophil recruitment
Januario, Jaqueline P.,De Souza, Thiago B,Lavorato, Stefania N.,Maiolini, Tatiane C. S.,Domingos, Olívia S,Baldim, Jo?o L,Folquitto, Laís R. S.,Soares, Marisi G.,Chagas-Paula, Daniela A,Dias, Danielle F,Dos Santos, Marcelo H
, (2018/08/04)
A series of novel benzophenone derivatives containing a thiazole heterocyclic nucleus were designed by molecular hybridization. Molecular docking studies have demonstrated the inhibitory potential of the designed compounds against cyclooxygenase (COX) isoenzymes. These compounds were synthesized, characterized, and evaluated for their anti-inflammatory properties by the croton oil-induced ear edema assay to examine their effect on both prostaglandin (PG) production and neutrophils recruitment. The thiazole derivatives displayed a potent effect in terms of reducing ear edema. The analysis suggested that the presence of 4-phenyl-2-hydrazinothiazole and the absence of C40-OCH3 on the benzophenone derivative structure are strongly related to the inhibition of PG production. In addition, the derivatives 2e, 3a and 3c concomitantly inhibit PG production and neutrophil recruitment, which may be a mechanism of action better than of common NSAIDs due to their inability to inhibit the neutrophil recruitment. Thus, these compounds can be considered as potential lead compounds toward the development of new anti-inflammatory drugs with an innovating mechanism of action.
Pharmaceutical intermediate p-benzoylbenzoic acid synthesis method
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Paragraph 0013; 0016-0027, (2018/07/30)
The invention discloses a pharmaceutical intermediate p-benzoylbenzoic acid synthesis method, which comprises: adding 3-amino-4-hydroxymethyl benzophenone and a potassium nitrate solution into a reaction container, controlling the stirring speed, increasing the temperature of the solution, adding a 2-methyl-1-butanol solution, adding terbium oxide powder in batches, maintaining reflux after completing the adding, adding a potassium bromide solution, precipitating the crystal, filtering, washing multiple times with an o-xylene solution, washing multiple times with a hexachlorethane solution, re-crystallizing in a sulfuryl chloride solution, and dehydrating with a dehydrating agent to obtain the finished product p-benzoylbenzoic acid.
Efficient N-heterocyclic carbene palladium(II) catalysts for carbonylative Suzuki-Miyaura coupling reactions leading to aryl ketones and diketones
Ibrahim, Mansur,Malik, Imran,Mansour, Waseem,Sharif, Muhammad,Fettouhi, Mohammed,El Ali, Bassam
, p. 44 - 51 (2018/02/14)
New N, N′-substituted imidazolium salts (L1 and L2) and their corresponding diiodopyridinepalladium(II) complexes (C1 and C2) were successfully synthesized and characterized. Reactions of palladium iodide with the newly synthesized N, N′-substituted imidazolium iodides in pyridine afforded the corresponding new palladium-N-heterocyclic carbene pyridine complexes in high yields. The new palladium(II) complex C1 was characterized by single crystal X-ray diffraction analysis. The Pd(II) ion is bonded to the nitrogen atom of the pyridine, the carbon atom of the NHC carbene ligand and two trans iodides resulting in distorted square planar geometry. The two Pd-NHC-Py complexes C1 and C2 displayed higher catalytic activity in the carbonylative Suzuki-Miyaura coupling reactions with much lower catalyst loading as compared to the catalytic systems reported in the literature.
