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Acetyl nitrate mediated conversion of methyl ketones to diverse carboxylic acid derivatives
The development of a novel acetyl nitrate mediated oxidative conversion of methyl ketones to carboxylic acid derivatives is described. By analogy to the haloform reaction and supported by experimental and computational investigation we propose a mechanism for this transformation.
Bernard, Josephine,Capilato, Joseph N.,Hoy, Erik P.,Mattiucci, Joseph,Pellegrinelli, Peter J.,Perez, Lark J.,Philippi, Shane,Schnorbus, Logan
p. 5298 - 5302
(2021/06/30)

Aerobic oxidation of aldehydes to carboxylic acids catalyzed by recyclable ag/c3 n4 catalyst
The oxidation of aldehydes is an efficient methodology for the synthesis of carboxylic acids. Herein we hope to report a simple, efficient and recyclable protocol for aerobic oxidation of aldehydes to carboxylic acid by using C3N4 supported silver nanoparticles (Ag/C3N4) as a catalyst in aqueous solution under mild conditions. Under standard conditions, the corresponding carboxylic acids can be obtained in good to excellent yields. In addition, Ag/C3N4 is convenient for recovery and could be reused three times with satisfactory yields.
Wu, Chaolong,Yao, Xiaoquan,Yu, Min,Zhou, Li,Zhu, Li
p. 167 - 175
(2021/03/19)

Efficiency of lithium cations in hydrolysis reactions of esters in aqueous tetrahydrofuran
Lithium cations were observed to accelerate the hydrolysis of esters with hydroxides (KOH, NaOH, LiOH) in a water/tetrahydrofuran (THF) two-phase system. Yields in the hydrolysis of substituted benzoates and aliphatic esters using the various hydroxides were compared, and the effects of the addition of lithium salt were examined. Moreover, it was presumed that a certain amount of LiOH was dissolved in THF by the coordination of THF with lithium cation and hydrolyzed esters even in the THF layer, as in the reaction by a phase-transfer catalyst.
Harada, Yumi,Hayashi, Kazuhiko,Ichimaru, Yoshimi,Imai, Masanori,Kojima, Yuki,Maeda, Azusa,Nakayama, Kanae,Sugiura, Kirara
p. 581 - 594
(2021/06/06)

Selective oxidation of alkenes to carbonyls under mild conditions
Herein, a practical and sustainable method for the synthesis of aldehydes, ketones, and carboxylic acids from an inexpensive olefinic feedstock is described. This transformation features very sustainable and mild conditions and utilizes commercially available and inexpensive tetrahydrofuran as the additive, molecular oxygen as the sole oxidant and water as the solvent. A wide range of substituted alkenes were found to be compatible, providing the corresponding carbonyl compounds in moderate-to-good yields. The control experiments demonstrated that a radical mechanism is responsible for the oxidation reaction.
Huo, Jie,Xiong, Daokai,Xu, Jun,Yue, Xiaoguang,Zhang, Pengfei,Zhang, Yilan
supporting information
p. 5549 - 5555
(2021/08/16)

Cleavage of Carboxylic Esters by Aluminum and Iodine
A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.
Sang, Dayong,Yue, Huaxin,Fu, Yang,Tian, Juan
p. 4254 - 4261
(2021/03/09)

Light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C-H bonds
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
Fu, Hua,Liu, Can,Liu, Yong,Yang, Haijun,Zhu, Xianjin
supporting information
p. 4357 - 4363
(2020/07/14)

Catalytic C-H aerobic and oxidant-induced oxidation of alkylbenzenes (including toluene derivatives) over VO2+immobilized on core-shell Fe3O4?SiO2at room temperature in water
Direct C-H bond oxidation of organic materials, and producing the necessary oxygenated compounds under mild conditions, has attracted increasing interest. The selective oxidation of various alkylbenzenes was carried out by means of a new catalyst containing VO2+ species supported on silica-coated Fe3O4 nanoparticles using t-butyl hydroperoxide as an oxidant at room temperature in H2O or solvent-free media. The chemical and structural characterization of the catalyst using several methods such as FTIR spectroscopy, XRD, FETEM, FESEM, SAED, EDX and XPS showed that VO2+ is covalently bonded to the silica surface. High selectivity and excellent conversion of various toluene derivatives, with less reactive aliphatic (sp3) C-H bonds, to related benzoic acids were quite noticeable. The aerobic oxygenation reaction of these alkylbenzenes was studied under the same conditions. All the results accompanied by sustainability of the inexpensive and simple magnetically separable heterogeneous catalyst proved the important criteria for commercial applications. This journal is
Mohammadpour, Pegah,Safaei, Elham
p. 23543 - 23553
(2020/07/14)

Photoinduced Carbon Tetrabromide Initiated Aerobic Oxidation of Substituted Toluenes to Carboxylic Acids
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.
Li, Xiaoqing,Xu, Xiangsheng,Yan, Xiaoyu,Yan, Xinhuan,Zhang, Guofu,Zheng, Kun
p. 272 - 274
(2020/02/18)

Method for preparing organic acid by oxidative cleavage of aromatic secondary alcohol
The invention relates to a method for preparing organic acids by oxidation of aromatic secondary alcohols. With air or oxygen as an oxygen source, a copper salt and an organic ligand as catalysts, aninorganic alkali is added, and aromatic secondary alcohols are subjected to carbon-carbon bond oxidative cracking to obtain the organic acids. The method has the advantages of high oxidation efficiency and high product yield; with the use of air or oxygen as the oxygen source, the method is economical and environmentally friendly and has good application prospects.
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Paragraph 0043-0046; 0051

(2020/09/16)

Preparation method of bimetallic catalyst oxidation aldehyde synthetic carboxylic acid (by machine translation)
The method is, in a reaction solvent: under normal pressure oxygen condition, under the action of a bimetallic catalyst under the action of a bimetallic catalyst under the action of a bimetallic catalyst under the action of a bimetallic catalyst, at, DEG, under stirring . under a stirring condition with an aldehyde compound as a substrate 10-90 °C in a reaction solvent under, a stirring condition under the action of a bimetallic catalyst . The reaction solution is stirred, for. 1-12h, hours at; room temperature, under, the action, of a bimetallic 1:1 catalyst Cu(OAc) under the action of a bimetallic catalyst under the action of a bimetallic catalyst under the action of a double-metal catalyst. 2 · H2 O And Co(OAc)2 · 44H2 O As the bimetallic catalyst, can achieve the highest yield of the carboxylic acid product, in high yield, by adjusting the reaction temperature, solvent, catalyst amount, for different types of the raw material aldehyde 98%. (by machine translation)
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Paragraph 0038-0039

(2020/05/30)

A Woven Supramolecular Metal-Organic Framework Comprising a Ruthenium Bis(terpyridine) Complex and Cucurbit[8]uril: Enhanced Catalytic Activity toward Alcohol Oxidation
The self-assembly of a diamondoid woven supramolecular metal–organic framework wSMOF-1 has been achieved from intertwined [Ru(tpy)2]2+ (tpy=2,2′,6′,2′′-terpyridine) complex M1 and cucurbit[8]uril (CB[8]) in water, where the intermolecular dimers formed by the appended aromatic arms of M1 are encapsulated in CB[8]. wSMOF-1 exhibits ordered pore periodicity in both water and the solid state, as confirmed by a combination of 1H NMR spectroscopy, UV-vis absorption, isothermal titration calorimetry, dynamic light scattering, small angle X-ray scattering and selected area electron diffraction experiments. The woven framework has a pore aperture of 2.1 nm, which allows for the free access of both secondary and primary alcohols and tert-butyl hydroperoxide (TBHP). Compared with the control molecule [Ru(tpy)2]Cl2, the [Ru(tpy)2]2+ unit of wSMOF-1 exhibits a remarkably higher heterogeneous catalysis activity for the oxidation of alcohols by TBHP in n-hexane. For the oxidation of 1-phenylethan-1-ol, the yield of acetophenone was increased from 10 percent to 95 percent.
Li, Zhan-Ting,Liu, Yi,Wang, Hui,Wang, Ze-Kun,Xu, Zi-Yue,Zhang, Dan-Wei,Zhang, Yun-Chang
p. 1498 - 1503
(2020/08/05)

A sodium trifluoromethanesulfinate-mediated photocatalytic strategy for aerobic oxidation of alcohols
A sodium trifluoromethanesulfinate-mediated photocatalytic strategy for the aerobic oxidation of alcohols has been developed for the first time, and the photoredox aerobic oxidation of secondary and primary alcohols provided the corresponding ketones and carboxylic acids, respectively, in high to excellent yields.
Zhu, Xianjin,Liu, Can,Liu, Yong,Yang, Haijun,Fu, Hua
p. 12443 - 12446
(2020/10/30)

Copper (II) immobilized on magnetically separable L-arginine-β-cyclodextrin ligand system as a robust and green catalyst for direct oxidation of primary alcohols and benzyl halides to acids in neat conditions
Copper (II) immobilized on L-arginine-β-cyclodextrin-functionalized magnetite nanoparticles (nano-Fe3O4@L-arginine-CD-Cu(II)) were successfully synthesized and fully characterized using FT-IR, XRD, SEM, EDX, ICP, TGA and VSM techniques. The catalytic activity of these magnetically retrievable nanoparticles was evaluated in the direct oxidation of primary alcohols and benzyl halides to acids in neat conditions that was observed to proceed well and products were obtained in good yields. In addition to showing good catalytic activity, the magnetic catalyst is easy to synthesize and can be recycled at least five times with little loss in activity.
Nejad, Masoumeh Jadidi,Salamatmanesh, Arefe,Heydari, Akbar
(2020/02/11)

Synthesis method of benzoic acid compounds
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.
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Paragraph 0110; 0111; 0112; 0113

(2019/12/25)

Method for copper-catalyzed carboxylation reaction of arylboronic acid and carbon dioxide
The invention discloses a method for a copper-catalyzed carboxylation reaction of arylboronic acid and carbon dioxide. According to the method, carbon dioxide is used as a C1 source, copper catalysisis adopted, alkoxide serves as alkali, and a reaction is carried out in an organic solvent; the method is simple in process and easy to implement, and shows wide functional group compatibility; the method allows various arylboronic acids such as monosubstituted or polysubstituted phenylboronic acid, polycyclic aromatic hydrocarbon boronic acid and benzoheterocyclic boronic acid to be converted into corresponding arylcarboxylic acids with considerable yield under mild conditions; and the produced carboxylic acids have important application value, and can be used for deriving a great number of other common chemical substances, such as acyl halide, acid anhydride, ester and amide.
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Paragraph 0037; 0038

(2019/12/29)

Picolinamide Assisted Oxidation of CH2 Groups Bound to Organic and Organometallic Compounds Using Ferrocene as a Catalyst
Picolinamide group assisted sp3 C-H bond oxidation of methylene groups to the corresponding carbonyl compounds has been achieved by using simple bottle ferrocene as catalyst and Cu(OAc)2 or tert-butyl peroxybenzoate (TBPB) as oxidant under mild conditions. This method is applicable for picolinamide bound organic as well as organometallic compounds with yields in the range of 46-82%. Control experiments and mechanistic studies indicate that a radical mechanism is responsible for these oxidative transformations in which ferrocene acts as a catalyst.
Dolui, Pritam,Hazra, Susanta,Deb, Mayukh,Elias, Anil J.
p. 2015 - 2021
(2019/05/16)

Heteropolyacid immobilized on polymer/magnetic zeolite nanocomposite as a new and recyclable catalyst for the selective oxidation of alcohols
A new magnetic oxidation catalyst was prepared using immobilization of tungstophosphoric acid on poly(N-vinylimidazole) entrapped magnetic nanozeolite and characterized by FTIR, TGA, XRD, SEM, TEM, EDX, VSM, and ICP-OES. The resulting heterogeneous catalyst displays high catalytic performance for selective oxidation of alcohols compared to the other catalysts. The catalyst could be reused eight times without any loss of catalytic activity.
Maleki, Maryam,Baghbanian, Seyed Meysam,Tajbakhsh, Mahmood
p. 359 - 368
(2018/03/29)

The Cu(I)- and HNO3-catalyzed oxidation of substituted toluenes to the benzoic acid based on NOx recycling
Based on the recycling of NOx, the Cu(I)- and HNO3-catalyzed oxidation of 2-chloro-4-(methylsulfonyl)toluene to 2-chloro-4-(methylsulfonyl)benzoic acid has been developed with an excellent yield of 84.2% and a purity of 99.7%. The optimized reaction conditions (160?°C, oxygen pressure 1.5?MPa, HNO3 concentration 25?wt%, HNO3: substrate 0.5:1) use 1.0?mol% CuI as catalyst. The dosage of HNO3 in the new process is only 25% of the stoichiometric amount and 12.5% of the amount of the traditional process. The NOx emission is 5% amount of the traditional process. The oxidation of several additional toluene derivatives with comparable yields demonstrates the generality to these reaction conditions.
Wei, Mengyi,Qian, Chao,Chen, Xinzhi
p. 51 - 56
(2018/01/17)

Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N-Halosuccinimide
A one-pot universal approach for transforming arylamines to aryl halides via reaction with sodium nitrite (NaNO2) and N-halosuccinimide (NXS) in DMF at room temperature under metal- and acid-free condition is described. This new protocol that is complementary to the Sandmeyer reaction, is suggested to involve the in situ generation of nitryl halide induce nitrosylation of aryl amine to form the diazo intermediate which is halogenated to furnish the aryl halide.
Mukhopadhyay, Sushobhan,Batra, Sanjay
supporting information
p. 14622 - 14626
(2018/09/21)

A biocatalytic method for the chemoselective aerobic oxidation of aldehydes to carboxylic acids
Herein, we present a study on the oxidation of aldehydes to carboxylic acids using three recombinant aldehyde dehydrogenases (ALDHs). The ALDHs were used in purified form with a nicotinamide oxidase (NOx), which recycles the catalytic NAD+ at the expense of dioxygen (air at atmospheric pressure). The reaction was studied also with lyophilised whole cell as well as resting cell biocatalysts for more convenient practical application. The optimised biocatalytic oxidation runs in phosphate buffer at pH 8.5 and at 40 °C. From a set of sixty-one aliphatic, aryl-Aliphatic, benzylic, hetero-Aromatic and bicyclic aldehydes, fifty were converted with elevated yield (up to >99%). The exceptions were a few ortho-substituted benzaldehydes, bicyclic heteroaromatic aldehydes and 2-phenylpropanal. In all cases, the expected carboxylic acid was shown to be the only product (>99% chemoselectivity). Other oxidisable functionalities within the same molecule (e.g. hydroxyl, alkene, and heteroaromatic nitrogen or sulphur atoms) remained untouched. The reaction was scaled for the oxidation of 5-(hydroxymethyl)furfural (2 g), a bio-based starting material, to afford 5-(hydroxymethyl)furoic acid in 61% isolated yield. The new biocatalytic method avoids the use of toxic or unsafe oxidants, strong acids or bases, or undesired solvents. It shows applicability across a wide range of substrates, and retains perfect chemoselectivity. Alternative oxidisable groups were not converted, and other classical side-reactions (e.g. halogenation of unsaturated functionalities, Dakin-Type oxidation) did not occur. In comparison to other established enzymatic methods such as the use of oxidases (where the concomitant oxidation of alcohols and aldehydes is common), ALDHs offer greatly improved selectivity.
Knaus, Tanja,Tseliou, Vasilis,Humphreys, Luke D.,Scrutton, Nigel S.,Mutti, Francesco G.
supporting information
p. 3931 - 3943
(2018/09/11)

Catalytic Promiscuity of Galactose Oxidase: A Mild Synthesis of Nitriles from Alcohols, Air, and Ammonia
We report an unprecedented catalytically promiscuous activity of the copper-dependent enzyme galactose oxidase. The enzyme catalyses the one-pot conversion of alcohols into the related nitriles under mild reaction conditions in ammonium buffer, consuming ammonia as the source of nitrogen and dioxygen (from air at atmospheric pressure) as the only oxidant. Thus, this green method does not require either cyanide salts, toxic metals, or undesired oxidants in stoichiometric amounts. The substrate scope of the reaction includes benzyl and cinnamyl alcohols as well as 4- and 3-pyridylmethanol, giving access to valuable chemical compounds. The oxidation proceeds through oxidation from alcohol to aldehyde, in situ imine formation, and final direct oxidation to nitrile.
Vilím, Jan,Knaus, Tanja,Mutti, Francesco G.
supporting information
p. 14240 - 14244
(2018/10/15)

Tandem one-pot CO2 reduction by PMHS and silyloxycarbonylation of aryl/vinyl halides to access carboxylic acids
The present study discloses the synthesis of aryl/vinyl carboxylic acids from Csp2-bound halides (Cl, Br, I) in a carbonylative path by using silyl formate (from CO2 and hydrosilane) as an instant CO-surrogate. Hydrosilane provides hydride for reduction and its oxidation product silanol serves as a coupling partner. Mono-, di-, and tri-carboxylic acids were obtained from the corresponding aryl/vinyl halides.
Paridala, Kumaraswamy,Lu, Sheng-Mei,Wang, Meng-Meng,Li, Can
supporting information
p. 11574 - 11577
(2018/10/31)

An optimized procedure for direct access to 1: H -indazole-3-carboxaldehyde derivatives by nitrosation of indoles
Indazole derivatives are currently drawing more and more attention in medicinal chemistry as kinase inhibitors. 1H-indazole-3-carboxaldehydes are key intermediates to access to a variety of polyfunctionalized 3-substituted indazoles. We report here a general access to this motif, based on the nitrosation of indoles in a slightly acidic environment. These very mild conditions allow the conversion of both electron-rich and electron-deficient indoles into 1H-indazole-3-carboxaldehydes.
Chevalier, Arnaud,Ouahrouch, Abdelaaziz,Arnaud, Alexandre,Gallavardin, Thibault,Franck, Xavier
p. 13121 - 13128
(2018/04/23)

Oxalic acid as the: In situ carbon monoxide generator in palladium-catalyzed hydroxycarbonylation of arylhalides
An efficient palladium-catalyzed hydroxycarbonylation reaction of arylhalides using oxalic acid as a CO source has been developed. The reaction features high safety, low catalyst loading, and a broad substrate scope, and provides a safe and tractable approach to access a variety of aromatic carboxylic acid compounds. Mechanistic studies revealed the decomposition pattern of oxalic acid.
Shao, Changdong,Lu, Ailan,Wang, Xiaoling,Zhou, Bo,Guan, Xiaohong,Zhang, Yanghui
supporting information
p. 5033 - 5040
(2017/07/10)

Harnessing the Reactivity of Iridium Hydrides by Air: Iridium-Catalyzed Oxidation of Aldehydes to Acids in Water
An iridium-catalyzed oxidation of aldehydes to acids was realized by using air as the oxidant and water as the solvent in the presence of base. Interestingly, the same type of catalysts were also used for the reduction of aldehydes under acidic conditions. A common iridium hydride intermediate is proposed for both redox reactions. The oxidation has a number of advantages such as high yields, great functionality tolerance, and easy purification without chromatography.
Yang, Zhanhui,Luo, Renshi,Zhu, Zhongpeng,Yang, Xuerong,Tang, Weiping
supporting information
p. 4095 - 4098
(2017/11/21)

Dehydrogenative oxidation of alcohols in aqueous media catalyzed by a water-soluble dicationic iridium complex bearing a functional N-heterocyclic carbene ligand without using base
A dicationic iridium complex bearing a bidentate ligand that comprises N-heterocyclic carbene and α-hydroxypyridine moieties has been designed and synthesized. The complex exhibited high catalytic performance in aqueous media for the dehydrogenative oxidation of secondary alcohols to ketones accompanying the evolution of hydrogen. Furthermore, dehydrogenative transformation of primary alcohols to the carboxylic acids in aqueous media was also catalyzed by the complex without using base.
Fujita, Ken-Ichi,Tamura, Ryuichi,Tanaka, Yuhi,Yoshida, Masato,Onoda, Mitsuki,Yamaguchi, Ryohei
p. 7226 - 7230
(2017/11/09)

Oxidant-Controlled C-sp2/sp3-H Cross-Dehydrogenative Coupling of N-Heterocycles with Benzylamines
Oxidant controlled ionic liquid mediated cross-dehydrogenative coupling (CDC) of benzylamines with N-heterocycles having sp2 or sp3 carbon resulted in the formation of C-benzoylated or alkenylated products. Benzoylation of N-heterocycles occurs via (NH4)2S2O8 catalyzed benzoyl radical formation. An oxidative alkenylation of N-heterocycles having C-sp3 carbon (2-methylaza-arenes) occurs via deamination of benzylamine followed by C-sp3-H bond activation in high stereoselectivity. Both benzoylation and alkenylation protocols are metal-free, green, simple, efficient, and tolerate a wide variety of functional groups.
Sharma, Rohit,Abdullaha, Mohd,Bharate, Sandip B.
p. 9786 - 9793
(2017/09/23)

Iodine-catalyzed oxidative C-C bond cleavage for benzoic acids and benzamides from alkyl aryl ketones
Iodine-catalyzed oxidative C-C bond cleavage has been performed for the facile synthesis of both benzoic acids and benzamides from readily available alkyl aryl ketones. Additionally benzylidene acetones and phenylacetylenes were also converted to the corresponding aromatic acids under the same conditions. This approach features the use of inexpensive iodine as a catalyst, broad substrate scope and open air conditions.
Sathyanarayana, Pochampalli,Upare, Atul,Ravi, Owk,Muktapuram, Prathap Reddy,Bathula, Surendar Reddy
p. 22749 - 22753
(2016/03/15)

Promising hydrogen peroxide stabilizers for large-scale application: unprecedented effect of aryl alkyl ketones
Aryl alkyl ketones with substituents in the aromatic ring taken in an amount from 0.005 to 0.5% efficiently stabilize hydrogen peroxide in an aqueous solution during storage at 22–25°C for 16–24 months.
Terent'ev, Alexander O.,Pastukhova, Zhanna Yu.,Yaremenko, Ivan A.,Bruk, Lev G.,Nikishin, Gennady I.
p. 329 - 331
(2016/08/09)

With anti-tumor activity of a biphenyl amide compound and its preparation method and application
The invention discloses a diphenyl amide compound with anti-tumor activity as well as a preparation method and an application of the diphenyl amide compound. The structural formula of the compound is shown in the specification, wherein R1 is hydrogen or halogen, R2 is alkoxyl which is substituted by tertiary amino at the tail end and has 1-4 carbon atoms and R2 is connected to the para-position of amide through oxygen atoms. The compound has good inhibiting activity to tumor cells in vitro and can be used for preparing anti-tumor medicines, particularly anti-liver cancer medicines and anti-breast cancer medicines. The preparation method of the diphenyl amide compound has the advantages of easily available raw materials, mild reaction condition, simple reaction operation process and cheap used reagents.
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Paragraph 0050; 0051

(2016/10/07)

Combined production method for substituted benzaldehyde, substituted benzyl alcohol and substituted benzoic acid
The invention discloses a combined production method for substituted benzaldehyde, substituted benzyl alcohol and substituted benzoic acid. The method comprises the following steps: (1) oxidation: a step of continuously introducing substituted toluene, a catalyst and oxygen-contained gas into an oxidation reactor and carrying out reaction so as to obtain oxidation reaction liquid; (2) hydrolyzation: a step of allowing the oxidation reaction liquid to continuously enter a hydrolysis reactor, and continuously adding water into the hydrolysis reactor and carrying out reaction so as to obtain a hydrolysis reaction mixture; (3) liquid-liquid layering: a step of layering the hydrolysis reaction mixture so as to obtain an oil phase and an aqueous phase; and (4) separation of products: a step of subjecting the oil phase to distillation so as to respectively obtain incompletely-reacted substituted toluene, substituted benzyl alcohol and substituted benzaldehyde, and subjecting the aqueous phase to cooling, crystallizing and filtering so as to obtain filtrate and substituted benzoic acid. The combined production method provided by the invention has the advantages of high raw material conversion rate, few by-products, good selectivity of target products, greenness and environmental protection.
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Paragraph 0095; 0096

(2017/01/31)

Direct regioselective Csp2-H trifluoromethylation of pyrimidinones and pyridinones
A direct regioselective Csp2-H trifluoromethylation of pyrimidinones and pyridinones using CF3SO2Na/Mn(OAc)3 to afford 5-trifluoromethyl pyrimidinones and 3-trifluoromethyl pyridinones in moderate to good yields was described. The reaction showed that the steric hindrance due to bulky groups adjacent to the position of attack by the trifluoromethyl radical had important influence on the yield.
Zhang, Pei-Zhi,Li, Cheng-Kun,Zhang, Guo-Yu,Zhang, Ling,Jiang, Yao-Jia,Zou, Jian-Ping
p. 3250 - 3255
(2016/05/24)

Iron-Catalysed Selective Aerobic Oxidation of Alcohols to Carbonyl and Carboxylic Compounds
A method for aerobic alcohol oxidation catalysed by Fe(NO3)3/2,2’-bipyridine/TEMPO has allowed highly selective conversion of primary alcohols into either aldehydes or carboxylic acids in one-step. The oxidation of primary alcohols proceeded selectively to aldehydes, as TEMPO was present in the reaction. Nevertheless, the aldehydes were further oxidized into carboxylic acids as the reaction time was extended. Detailed investigation of the reaction suggested, that the deoxygenation of TEMPO into TMP enabled the auto-oxidation of aldehydes to carboxylic acids, which was initially inhibited in the presence of TEMPO. The procedure was also efficient in oxidation of secondary alcohols when TEMPO was replaced by the less sterically hindered ABNO.
Lagerblom, Kalle,Wrigstedt, Pauli,Keskiv?li, Juha,Parviainen, Arno,Repo, Timo
p. 1160 - 1165
(2016/11/23)

Ultrasmall Platinum Nanoparticles Supported Inside the Nanospaces of Periodic Mesoporous Organosilica with an Imidazolium Network: An Efficient Catalyst for the Aerobic Oxidation of Unactivated Alcohols in Water
The imidazolium group inside the wall of a periodic mesoporous organosilica provides an excellent environment for the stabilization of ultrasmall Pt nanoparticles ((NP)@PMO-IL) with significant activity and recyclability in the selective aerobic oxidation of various alcohols in water at ambient pressure of oxygen. In particular, the catalyst exhibited high activity in the oxidation of unactivated primary alcohols and sterically encumbered secondary aliphatic alcohols, which remain challenging substrates for many catalytic aerobic protocols.
Karimi, Babak,Naderi, Zahra,Khorasani, Mojtaba,Mirzaei, Hamid M.,Vali, Hojatollah
p. 906 - 910
(2016/03/15)

Copper catalyzed oxygen assisted C(CNOH)-C(alkyl) bond cleavage: A facile conversion of aryl/aralkyl/vinyl ketones to aromatic acids
A novel copper-catalyzed aerobic oxidative C(NOH)-C(alkyl) bond cleavage reaction of aryl/aralkyl/vinyl ketones for the synthesis of aromatic/acrylic acids is described. A series of ketones having aryl/aralkyl/vinyl at the one end and methyl to any higher alkyl at the other end can be selectively cleaved and converted into the corresponding acids via oxime intermediates.
Sathyanarayana, Pochampalli,Ravi, Owk,Muktapuram, Prathap Reddy,Bathula, Surendar Reddy
supporting information
p. 9681 - 9685
(2015/09/28)

Discovery of biphenyl-based VEGFR-2 inhibitors. Part 3: Design, synthesis and 3D-QSAR studies
VEGFR-2 plays an essential role in angiogenesis and is a central target for anticancer drug discovery. In order to develop novel VEGFR-2 inhibitors, we designed and synthesized 33 biphenyl amides based on our previously reported lead compound. The biological results indicated that four compounds (18b, 20e, 20h and 20j) are potent VEGFR-2 inhibitors which are comparable to positive control. Compound 18b displayed the most potent VEGFR-2 inhibition with IC50 value of 2.02 nM. Moreover, it exhibited promising antiproliferative activity against MCF-7 and SMMC-7721 cells with IC50 values of 1.47 μM and 5.98 μM, respectively. Molecular docking and 3D-QSAR studies were also carried out. The results indicated that these biphenyl amides could serve as promising leads for further optimization as novel VEGFR-2 inhibitors.
Lu, Wen,Li, Pengfei,Shan, Yuanyuan,Su, Ping,Wang, Jinfeng,Shi, Yaling,Zhang, Jie
p. 1044 - 1054
(2015/03/04)

Synthesis of benzoyl cyanide through aerobic photooxidation of benzyl cyanide using carbon tetrabromide as a catalyst
We developed a synthetic method toward benzoyl cyanide through aerobic photooxidation of benzyl cyanide in the presence of carbon tetrabromide under visible light irradiation with fluorescent lamps.
Sugiura,Tachikawa,Nagasawa,Tada,Itoh
p. 70883 - 70886
(2015/09/08)

Nucleophilic aromatic cine-substitution of hydrogen: The ionic liquid-promoted von Richter reaction
Conversion of 4-R-nitrobenzenes into 3-R-benzoic acids under the action of KCN in the EtOH-H2O mixture (the von Richter reaction) is significantly accelerated by ionic liquids thus allowing to extend the scope of the reaction. The finding is pi
Epishina, Margarita A.,Kulikov, Alexander S.,Ignat'ev, Nikolai V.,Schulte, Michael,Makhova, Nina N.
p. 41 - 43
(2015/02/05)

TEMPO-mediated oxidation of primary alcohols to aldehydes under visible light and air
A homogeneous visible light photoredox TEMPO-mediated selective oxidation of primary alcohols to the corresponding carbonyl compounds was developed using molecular oxygen from air as the terminal oxidant. Ru(bpy)3(PF 6)2 (bpy: bipyridyl) and Ir(dtb-bpy)(ppy) 2(PF6) (dtb-bpy: 4,4′-di-tert-butyl-2,2′- bipyridyl; ppy: 2-phenylpyridine) were used as the sensitizers. A homogeneous visible light photoredox TEMPO-mediated selective oxidation of primary alcohols to the corresponding carbonyl compounds was developed. Molecular oxygen from air was the terminal oxidant. Copyright
Liu, Dongwang,Zhou, Hongxia,Gu, Xiangyong,Shen, Xiaoqin,Li, Pixu
supporting information
p. 117 - 122
(2014/03/21)

Nanoparticle-supported and magnetically recoverable organic-inorganic hybrid copper(ii) nanocatalyst: A selective and sustainable oxidation protocol with a high turnover number
A magnetically recoverable copper-based nanocatalyst was prepared from inexpensive starting materials. With a particle size between 20 to 30 nm, it was shown to catalyze the oxidation of benzylic alcohols. The catalyst exhibited a high turnover number (TON) and excellent selectivity. The catalyst was characterized by several techniques, such as XRD, HR-TEM, SAED, EDS, FT-IR, VSM, and BET surface area. Factors affecting the reaction parameters, such as the substrate to oxidant molar ratio, weight of the catalyst, reaction time, etc., were investigated in detail. The reusability of the catalyst was examined by conducting repeat experiments with the same catalyst; it was observed that the catalyst displayed no significant changes in its activity even after seven cycles for the aerobic, as well as for the peroxide, oxidation of benzyl alcohol. Furthermore, the heterogeneous nature, easy recovery, and reusability, makes the present protocol highly beneficial for addressing environmental concerns and industrial requirements. This journal is
Rathore, Puran Singh,Patidar, Rajesh,Thakore, Sonal
p. 41111 - 41121
(2014/12/10)

Pyridinium Chlorochromate catalyzed oxidation of Toluenes to aromatic carboxylic acids with molecular oxygen in sub-critical water
Oxidation of substituted toluenes in the presence of molecular oxygen with pyridinium chlorochromate in subcritical water under the nitrogen atmosphere at 120 °C to the corresponding substituted benzoic acids were investigated. Substituted toluenes were directly oxidized to their carboxylic acids in excellent yields (> 70 %).
Ozen, Recep
p. 941 - 942
(2014/06/09)

An insight into the mechanism of the aerobic oxidation of aldehydes catalyzed by N-heterocyclic carbenes
N-Heterocyclic carbene catalysis for the aerobic oxidation and esterification of aromatic aldehydes was monitored by ESI-MS (MS/MS) and the key intermediates were intercepted and characterized using the charge-tag strategy.
Bortolini,Chiappe,Fogagnolo,Giovannini,Massi,Pomelli,Ragno
supporting information
p. 2008 - 2011
(2014/03/21)

Electrophilicity and nucleophilicity of commonly used aldehydes
The present approach for determining the electrophilicity (E) and nucleophilicity (N) of aldehydes includes a kinetic study of KMNO4 oxidation and NaBH4 reduction of aldehydes. A transition state analysis of the KMNO4 promoted aldehyde oxidation reaction has been performed, which shows a very good correlation with experimental results. The validity of the experimental method has been tested using the experimental activation parameters of the two reactions. The utility of the present approach is further demonstrated by the theoretical versus experimental relationship, which provides easy access to E and N values for various aldehydes and offers an at-a-glance assessment of the chemical reactivity of aldehydes in various reactions. the Partner Organisations 2014.
Pratihar, Sanjay
p. 5781 - 5788
(2014/07/22)

Catalytic bio-chemo and bio-bio tandem oxidation reactions for amide and carboxylic acid synthesis
A catalytic toolbox for three different water-based one-pot cascades to convert aryl alcohols to amides and acids and cyclic amines to lactams, involving combination of oxidative enzymes (monoamine oxidase, xanthine dehydrogenase, galactose oxidase and laccase) and chemical oxidants (TBHP or CuI(cat)/H2O2) at mild temperatures, is presented. Mutually compatible conditions were found to afford products in good to excellent yields. This journal is
Bechi, Beatrice,Herter, Susanne,McKenna, Shane,Riley, Christopher,Leimkühler, Silke,Turner, Nicholas J.,Carnell, Andrew J.
supporting information
p. 4524 - 4529
(2014/12/11)

Tribromoisocyanuric acid in trifluoroacetic acid: An efficient system for smooth brominating of moderately deactivated arenes
Moderately deactivated arenes are efficiently brominated by the reaction with tribromoisocyanuric acid (0.34 mol equiv) in trifluoroacetic acid at room temperature in 48-85% isolated yield. This medium avoids the polybromination of the substrate, observed in the same reaction performed in 98% H 2SO4. Georg Thieme Verlag Stuttgart · New York.
De Almeida, Leonardo S.,De Mattos, Marcioc. S.,Esteves, Pierre M.
p. 603 - 606
(2013/04/10)

Nickel(II) catalyzed oxidation of aldehyde derivatives to their carboxylic acid or ester analogs
Diverse aromatic, aliphatic and conjugated aldehydes were converted to the corresponding carboxylic acid or methyl ester derivatives with 30 % H 2O2 as the oxidant in the presence of a catalytic amount of nickel(II) complex as precursor. Ni(II) complex was prepared from the reaction of methyl 2-{3-[(E)-4-oxopent-2-en-2-ylamino]propylamino}cyclopent-1- enecarbodithioate as a tetra-dentate ligand with Ni(II) acetate in 60 % yield and was tested for its catalytic activity in the oxidation reaction. The prepared complex was characterized on the basis of 1H NMR, FT-IR, MASS, and CHN analysis. Aldehydes were oxidized to their corresponding carboxylic acid in acetonitrile as solvent and were converted to methyl esters in methanol as solvent. For all substrates, a considerable rate enhancement was observed. The present methodology offers several advantages such as applicability to a wide range of aldehydes, convenient work-up, mild reaction conditions, and good yields and reasonable time of the reactions. Graphical Abstract: [Figure not available: see fulltext.]
Esfandiari, Hadi,Jameh-Bozorghi, Saeed,Esmaielzadeh, Sheida,Shafiee, Mohammad Reza Mohammad,Ghashang, Majid
p. 3319 - 3325
(2013/09/23)

SnO 2 nanoparticles: Preparation and evaluation of their catalytic activity in the oxidation of aldehyde derivatives to their carboxylic acid and sulfides to sulfoxide analogs
A variety of aromatic and aliphatic aldehydes were converted to the corresponding carboxylic acid derivatives with 30% H2O2 and tert-butyl hydroperoxide as the oxidant in the presence of a catalytic amount of SnO2 nanoparticles as a precursor. These nanoparticles were also used for the efficient catalytic oxidation of sulfides to sulfoxides using 30% H2O2. The present methodology offers several advantages such as applicability to a wide range of aldehydes/sulfides, convenient work-up, mild reaction conditions as well as good yields and reasonable time of the reactions. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
Dehbashi, Mohsen,Aliahmad, Mousa,Shafiee, Mohammad Reza Mohammad,Ghashang, Majid
p. 864 - 872
(2013/08/23)

Palladium-catalyzed synthesis of aromatic carboxylic acids with silacarboxylic acids
Aryl iodides and bromides were easily converted to their corresponding aromatic carboxylic acids via a Pd-catalyzed carbonylation reaction using silacarboxylic acids as an in situ source of carbon monoxide. The reaction conditions were compatible with a wide range of functional groups, and with the aryl iodides, the carbonylation was complete within minutes. The method was adapted to the double and selective isotope labeling of tamibarotene.
Friis, Stig D.,Andersen, Thomas L.,Skrydstrup, Troels
supporting information
p. 1378 - 1381
(2013/04/24)

Copper-catalyzed carboxylation of aryl iodides with carbon dioxide
A method for carboxylation of aryl iodides with carbon dioxide has been developed. The reaction employs low loadings of copper iodide/N,N,N′, N′-tetramethylethylenediamine (TMEDA) or N,N′- dimethylethylenediamine (DMEDA) catalyst, 1 atm of CO2, dimethylsulfoxide (DMSO) or dimethylacetamide (DMA) solvent, and proceeds at 25-70 C. Good functional group tolerance is observed, with ester, bromide, chloride, fluoride, ether, hydroxy, amino, and ketone functionalities tolerated. Additionally, hindered aryl iodides such as iodomesitylene can also be carboxylated
Tran-Vu, Hung,Daugulis, Olafs
p. 2417 - 2420
(2013/10/22)

Direct and selective benzylic oxidation of alkylarenes via C-H abstraction using alkali metal bromides
A direct benzylic oxidation of alkylarenes via C-H bond abstraction was developed using alkali metal bromides and oxidants under mild conditions. This reaction proceeded with excellent selectivity by thermal oxidation or photooxidation to provide a broad range of carbonyl compounds containing electron-deficient aryl carbonyl compounds in high yields.
Moriyama, Katsuhiko,Takemura, Misato,Togo, Hideo
supporting information; experimental part
p. 2414 - 2417
(2012/06/18)