cas 90-98-2, 4,4'-Dichlorobenzophenone | Articles data

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Leebrick,Ramsden
p. 2259
(1962)
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Electrochemical Aerobic Oxidative Cleavage of (sp3)C-C(sp3)/H Bonds in Alkylarenes
An electrochemistry-promoted oxidative cleavage of (sp3)C-C(sp3)/H bonds in alkylarenes was developed. Various aryl alkanes can be smoothly converted into ketones/aldehydes under aerobic conditions using a user-friendly undivided cell setup. The features of air as oxidant, scalability, and mild conditions make them attractive in synthetic organic chemistry.
Liu, Shuai,Liu, Zhong-Quan,Shen, Tong,Shen, Xu,Wang, Nengyong,Wu, Jintao,Yang, Le,Zhao, Jianyou
p. 3286 - 3295
(2022/03/14)

Organotellurium-catalyzed oxidative deoximation reactions using visible-light as the precise driving energy
Irradiated by visible light, the recyclable (PhTe)2-catalyzed oxidative deoximation reaction could occur under mild conditions. In comparison with the thermo reaction, the method employed reduced catalyst loading (1 mol% vs. 2.5 mol%), but afforded elevated product yields with expanded substrate scope. This work demonstrated that for the organotellurium-catalyzed reactions, visible light might be an even more precise driving energy than heating because it could break the Te–Te bond accurately to generate the active free radical catalytic intermediates without damaging the fragile substituents (e.g., heterocycles) of substrates. The use of O2 instead of explosive H2O2 as oxidant affords safer reaction conditions from the large-scale application viewpoint.
Deng, Xin,Qian, Rongrong,Zhou, Hongwei,Yu, Lei
supporting information
p. 1029 - 1032
(2020/10/23)

PhSe(O)OH/NHPI-catalyzed oxidative deoximation reaction using air as oxidant
A novel oxidative deoximation method was developed in this article. Compared with the reported organoselenium-catalyzed oxidative deoximation reaction, this reaction employed N-hydroxyphthalimide (NHPI) as the co-catalyst, so that the oxidative deoximation reaction could utilize air as oxidant in the green DMC solvent under mild reaction conditions. Control experiments and X-ray photoelectron spectroscopy (XPS) analysis results indicated that NHPI was essential for activating the catalytic organoselenium species. It could accelerate the activation of molecular oxygen in air to promote the reaction process. The reaction can avoid metal residues in product and is of potential application values in pharmaceutical industry due to the transition metal-free process.
Shi, Yaocheng,Wang, Feng,Yang, Chenggen,Yu, Lei
(2021/09/06)

AIBN initiated functionalization of the benzylic sp3 C[sbnd]H and C[sbnd]C bonds in the presence of dioxygen
A sp3 C[sbnd]H bond functionalization and C[sbnd]C bond cleavage were realized by AIBN/O2 catalyst system, providing a series of benzophenones under mild reaction conditions. The mechanistic study shows that a peroxide intermediate is involved in this transformation, and in the case of diphenylmethanes, the sp3 C[sbnd]C bond is cleaved through the peroxide rearrangement, which might provides a new way to cleave relatively strong C[sbnd]C bond and be applied to more general C[sbnd]C bond activation.
Hu, Yingying,Shao, Yu,Zhang, Shuwei,Yuan, Yuan,Sun, Zheng,Yuan, Yu,Jia, Xiaodong
supporting information

(2021/02/01)

The Origin of Catalytic Benzylic C?H Oxidation over a Redox-Active Metal–Organic Framework
Selective oxidation of benzylic C?H compounds to ketones is important for the production of a wide range of fine chemicals, and is often achieved using toxic or precious metal catalysts. Herein, we report the efficient oxidation of benzylic C?H groups in a broad range of substrates under mild conditions over a robust metal–organic framework material, MFM-170, incorporating redox-active [Cu2II(O2CR)4] paddlewheel nodes. A comprehensive investigation employing electron paramagnetic resonance (EPR) spectroscopy and synchrotron X-ray diffraction has identified the critical role of the paddlewheel moiety in activating the oxidant tBuOOH (tert-butyl hydroperoxide) via partial reduction to [CuIICuI(O2CR)4] species.
Carter, Joseph H.,Day, Sarah J.,Han, Xue,Kang, Xinchen,Kimberley, Louis,Li, Jiangnan,McInnes, Eric J. L.,Schr?der, Martin,Sheveleva, Alena M.,Smith, Gemma L.,Tang, Chiu C.,Tuna, Floriana,Yang, Sihai
supporting information
p. 15243 - 15247
(2021/06/08)

Preparation method 4,4 ' -difluorobenzophenone and intermediate thereof
The invention discloses 4-4' -difluorobenzophenone and a preparation method of an intermediate thereof. The preparation method of 4, 4 '- difluorobenzophenone comprises the following steps: S1: 4 - chlorobenzyl chloride and chlorobenzene react under first catalyst to obtain 4, 4' -dichlorophenylmethane. The first catalyst is Lewis acid and/or a molecular sieve with Lewis acid center. S2: The 4, 4 '-dichlorophenylmethane and oxidant are subjected to an oxidation reaction under the action second catalyst to obtain 4, 4' -dichlorobenzophenone. S3: The 4, 4' -dichlorobenzophenone and the alkali metal fluoride are subjected to a halogenation reaction to obtain the invention. The 4' - difluorobenzophenone and the intermediate thereof disclosed by the invention are high in selectivity, high in yield, low in raw material cost, mild in process condition, high in safety and wide in industrial prospect.
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Paragraph 0068; 0071-0072; 0075; 0078-0079; 0082; ...

(2021/09/01)

Nitrosoarene-Catalyzed HFIP-Assisted Transformation of Arylmethyl Halides to Aromatic Carbonyls under Aerobic Conditions
A rare metal-free nucleophilic nitrosoarene catalysis accompanied by highly hydrogen-bond-donor (HBD) solvent, 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP), organocatalytically converts arylmethyl halides to aromatic carbonyls. This protocol offers an effective means to access a diverse array of aromatic carbonyls with good chemoselectivity under mild reaction conditions. The activation of arylmethyl halides by HFIP to generate stable carbocation and autoxidation of in situ generated hydroxylamine to nitrosoarene in the presence of atmospheric O2 are the keys to success.
Pradhan, Suman,Sharma, Vishali,Chatterjee, Indranil
supporting information
p. 6148 - 6152
(2021/08/03)

Preparation method of benzophenone derivative
The invention provides a preparation method of a benzophenone derivative. The preparation method comprises the following step: subjecting a benzoic acid compound as shown in a formula I, a trichlorotoluene compound as shown in a formula II and a benzene compound as shown in a formula III to reacting under the catalysis of Fe2O3 to obtain the benzophenone derivative. According to the preparation method provided by the invention, the metal oxide Fe2O3 with higher stability and safety is used as a catalyst, so corrosion of materials to equipment is avoided, and the preparation method is more environment-friendly; according to the preparation method, the target product is obtained through one-step reaction, reaction conditions are mild, and a process is simple; and the main byproduct benzoic acid compound generated by the reaction can be recycled by washing, extracting and desolventizing in post-treatment, and then is used as a reaction raw material for preparing the benzophenone derivative again, so wastewater treatment cost is reduced, and resources are fully utilized.
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Paragraph 0066-0071

(2021/06/22)

Palladium imine-pyridine-imine complex immobilized on graphene oxide as a recyclable catalyst for the carbonylative homo-coupling of aryl halides
A heterogeneous 3-N,N,N-(II) Pd(OAc)2 catalyst was prepared from the reaction of Pd(OAc)2 with Si-Prn-N = C-Py-C = N-Prn-Si immobilized on graphene oxide (GO-Si-Prn-N = C-Py-C = N-Prn-Si-GO). The prepared catalyst was characterized by inductively coupled plasma optical emission spectroscopy, Fourier transform infrared (FT-IR) spectroscopy, Raman spectroscopy, energy dispersive X-ray spectroscopy, X-ray diffraction, UV-vis spectroscopy, BET surface area, scanning electron microscopy, transmission electron microscopy, and thermogravimetric analysis. The catalyst was employed as a heterogeneous catalyst for carbonylative homo-coupling of aryl iodides and bromides under carbon monoxide gas-free condition. Cr(CO)6 was used as the carbon monoxide source and the desired symmetrical diaryl ketones were achieved in good to excellent yields. Moreover, the catalyst was reused up to five consecutive cycles without significant loss of activity.
Niakan, Mahsa,Asadi, Zahra,Khosrozadeh, Fatemeh
p. 850 - 863
(2020/12/18)

Benzophenanthrene derivative and application thereof
The invention relates to a benzophenanthrene derivative and application thereof. The structural formula of the benzophenanthrene derivative is shown as a formula (I). The benzophenanthrene derivativeis a novel organic electroluminescent compound with a fused ring structure of indole, benzofuran and benzothienobenzophenanthrene, the intramolecular electron density is increased on the basis of benzophenanthrene, meanwhile, substituent groups are adjusted to increase the molecular steric hindrance, the pi-pi interaction between molecules is weakened, the internal quantum efficiency of moleculesis improved, and a shorter emission wavelength than conventional compounds is achieved. Meanwhile, the benzophenanthrene derivative hinders the generation of an organic intermolecular excitation-excitation compound and increases the internal electron density and stability, so that the effect and the service life of the organic electroluminescent device prepared from the benzophenanthrene derivative are obviously improved and prolonged.
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Paragraph 0070-0074

(2021/01/28)

Palladium nanoparticles on amino-modified silica-catalyzed C–C bond formation with carbonyl insertion
Abstract: A practical and heterogeneously catalyzed Stille, homo-coupling, and Suzuki carbonylation reaction has been reported using Pd nanoparticles supported on amino-vinyl silica-functionalized magnetic carbon nanotube (CNT@Fe3O4@SiO2-Pd) for the efficient synthesis of symmetrical and unsymmetrical diaryl ketones from aryl iodides. A wide variety of symmetrical and unsymmetrical diaryl ketones were obtained in high yields under CO gas-free conditions using Mo(CO)6 as an efficient carbonyl source. Considering the atom economy of Ph3SnCl, less than an equimolar amount can be applied in Stille transformation, which is of great importance due to the toxicity of organotin derivatives. Moreover, no phosphine ligand and external reducing agent were necessary in these coupling carbonylation reactions. This heterogeneous Pd catalyst offers high activity with very low palladium leaching. Finally, the catalyst can be reused and recycled for six steps without loss in activity, exhibiting good example of sustainable methodology. Graphic abstract: [Figure not available: see fulltext.].
Etemadi-Davan, Elham,Khalili, Dariush,Banazadeh, Ali Reza,Sadri, Ghazal,Arshad, Pourya
p. 1891 - 1903
(2021/02/01)

Fe-S Catalyst Generated in Situ from Fe(III)- And S3?--Promoted Aerobic Oxidation of Terminal Alkenes
An iron-sulfur complex formed by the simple mixture of FeCl3 with S3?- generated in situ from K2S is developed and applied to selective aerobic oxidation of terminal alkenes. The reaction was carried out under an atmosphere of O2 (balloon) and could proceed on a gram scale, expanding the application of S3?- in organic synthesis. This study also encourages us to explore the application of an Fe-S catalyst in organic reactions.
Ai, Jing-Jing,Huang, Cheng-Mi,Li, Jian,Liu, Bei-Bei,Rao, Weidong,Wang, Fei,Wang, Shun-Yi
supporting information
p. 4705 - 4709
(2021/06/28)

Photo-induced oxidative cleavage of C-C double bonds for the synthesis of biaryl methanoneviaCeCl3catalysis
A Ce-catalyzed strategy is developed to produce biaryl methanonesviaphotooxidative cleavage of C-C double bonds at room temperature. This reaction is performed under air and demonstrates high activity as well as functional group tolerance. A synergistic Ce/ROH catalytic mechanism is also proposed based on the experimental observations. This protocol should be the first successful Ce-catalyzed photooxidation reaction of olefins with air as the oxidant, which would provide inspiration for the development of novel Ce-catalyzed photochemical synthesis processes.
Xie, Pan,Xue, Cheng,Du, Dongdong,Shi, SanShan
supporting information
p. 6781 - 6785
(2021/08/20)

Ruthenium-on-Carbon-Catalyzed Facile Solvent-Free Oxidation of Alcohols: Efficient Progress under Solid-Solid (Liquid)-Gas Conditions
A protocol for the ruthenium-on-carbon (Ru/C)-catalyzed solvent-free oxidation of alcohols, which proceeds efficiently under solid-solid (liquid)-gas conditions, was developed. Various primary and secondary alcohols were transformed to corresponding aldehydes and ketones in moderate to excellent isolated yields by simply stirring in the presence of 10% Ru/C under air or oxygen conditions. The solvent-free oxidation reactions proceeded efficiently regardless of the solid or liquid state of the substrates and reagents and could be applied to gram-scale synthesis without loss of the reaction efficiency. Furthermore, the catalytic activity of Ru/C was maintained after five reuse cycles.
Park, Kwihwan,Jiang, Jing,Yamada, Tsuyoshi,Sajiki, Hironao
p. 1200 - 1205
(2021/12/29)

Fe Doped MIL-101/Graphene Nanohybrid for Photocatalytic Oxidation of Alcohols Under Visible-Light Irradiation
A novel photoactive porous material of GR/FeMIL-101 based on FeMIL-101 metal organic frameworks (MOFs) was successfully synthesized via a simple hydrothermal method. The structural and photoelectric properties of the GR/FeMIL-101 was analyzed by XRD, SEM, TEM, TGA, XPS, UV–vis DRS, FT-IR, PL and EIS methods. The photocatalytic performance for the selective oxidation of benzyl alcohol with GR/FeMIL-101 as catalysts was evaluated under visible light irradiation. The results showed that the GR/FeMIL-101 nanohybrid had better photocatalytic performance than both of FeMIL-101 and the pristine MIL-101. It was further found that the incorporation of Fe and MIL-101 caused valence fluctuations of Fe3+/Fe2+ which improved the absorption of visible-light and increased the separation efficiency of photogenerated charges. In addition, the combination of FeMIL-101 and GR could further promote the transfer rate of the photoelectrons. The mechanism of the reaction revealed that ·O2? was the dominating active specie in this reaction through active species trapping experiments. Graphic Abstract: [Figure not available: see fulltext.]Fe doped MIL-101/GR nanohybrid was successfully synthesized as an efficient photocatalyst for selective oxidation of alcohols under visible-light and shown a best conversion of 50%. Analyses revealed that Fe was successfully doped into the MIL-101, valence fluctuation of Fe2+/Fe3+ not only improved the visible-light absorption but also increased the separation rate of photoexcited carriers. Graphene further improved the transportation rate of electron (e-). Subsequently, the possible photocatalytic mechanism for the selective oxidation of alcohols was proposed. It was proved that superoxide radicals (·O2-) was the main active species when the reaction was performed under Oxygen atmosphere.
Wang, Mingming,Ma, Yali,Lv, Bolin,Hua, Fenglin,Meng, Shuangyan,Lei, Xuedi,Wang, Qingtao,Su, Bitao,Lei, Ziqiang,Yang, Zhiwang
p. 2384 - 2395
(2021/01/04)

Oxidative C-S Bond Cleavage of Benzyl Thiols Enabled by Visible-Light-Mediated Silver(II) Complexes
The oxidative cleavage reaction of the C-S bond using singlet oxygen is challenging because of its uncontrollable nature. We have developed a novel method for the singlet-oxygen-mediated selective C-S bond cleavage reaction using silver(II)-ligand complexes. Visible-light-induced silver catalysis enables the controlled oxidative cleavage of benzyl thiols to afford carbonyl compounds, such as aldehydes or ketones, which are important synthetic components.
Hong, Boseok,Aganda, Kim Christopher C.,Lee, Anna
supporting information
p. 4395 - 4399
(2020/06/05)

A palladium-catalyzed C-H functionalization route to ketones: Via the oxidative coupling of arenes with carbon monoxide
We describe the development of a new palladium-catalyzed method to generate ketones via the oxidative coupling of two arenes and CO. This transformation is catalyzed by simple palladium salts, and is postulated to proceed via the conversion of arenes into high energy aroyl triflate electrophiles. Exploiting the latter can also allow the synthesis of unsymmetrical ketones from two different arenes.
Arndtsen, Bruce A.,Kinney, R. Garrison,Levesque, Taleah M.
p. 3104 - 3109
(2020/03/27)

Novel Friedel-Crafts reaction method and catalyst thereof
The present invention relates to a novel method for preparing or synthesizing an acylated or alkylated aryl compound, such as acylated or alkylated benzene, through a reaction called Friedel-Crafts, and a novel catalyst for the method. The present invention particularly relates to a novel environment-friendly method for synthesizing the Friedel-Crafts reaction of the acylated or alkylated compound.
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Paragraph 0167-0173

(2020/02/29)

NEW CYCLOADDUCT PRECURSORS OF DIHALOBENZOPHENONES AND PREPARATIONS THEREOF
The invention relates to new compounds of formula (I): wherein X represents a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine, which are useful for the preparation of 4,4' dihalobenzophenones of formula (III): wherein X is as defined above.
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Page/Page column 13-14

(2020/11/30)

PROCESS FOR THE PREPARATION OF DIHALOBENZOPHENONES, NEW CHEMICALS USEFUL FOR ITS IMPLEMENTATION AND METHODS FOR PREPARING SAID CHEMICALS
The invention relates to new compounds of formulae (IV), wherein X represents a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine, said compounds being useful as precursors and/or intermediates for the preparation of 4,4'dihalobenzophenones of formula (I), wherein X is as defined above.
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Paragraph 12; 13

(2020/12/01)

Iodobenzene-catalyzed oxidative cleavage of olefins to carbonyl compounds
A metal-free approach for the oxidative cleavage of carbon–carbon double bonds of olefins to carbonyl compounds was established by using oxidant m-CPBA and non-metallic organocatalyst PhI in toluene/H2O. A broad scope of aromatic olefins was used. All the reactions proceeded smoothly at 35 °C in short reaction time to furnish the respective mono- and double carbonyl compounds selectively in moderate to good yields.
Du, Lele,Wang, Zechao,Wu, Junliang
(2020/07/20)

Novel process for producing phenyl fluoride, diphenyl ketone fluoride, and derivatives thereof
The invention relates to a novel process for producing phenyl fluoride, diphenyl ketone fluoride, and derivatives thereof, especially the phenyl fluoride and derivatives thereof. The invention especially relates to a novel environment-friendly process for synthesizing phenyl fluoride and diphenyl ketone fluoride, which are the raw materials for preparing polyaryl-ether-ketone PAEK. The invention discloses the method that is more effective and environment-friendly for preparing the compounds through a Friedel-Crafts reaction, and further a more environment-friendly process, and provdies beneficial catalysts. Another object of the present invention is to employ the Friedel-Crafts reaction and adopts the beneficial catalysts, wherein the catalyst can be easily combined with the fluoridation reaction which can be carried out before, or after the Friedel-Crafts reaction. Herein, another object of the invention is to use the catalyst in the Friedel-Crafts reaction, wherein the catalyst can work in both the Friedel-Crafts reaction and the fluoridation reaction.
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(2020/07/02)

ε-Caprolactone manufacture via efficient coupling Baeyer-Villiger oxidation with aerobic oxidation of alcohols
To avoid the use of peracids oxidant or highly concentrated hydrogen peroxide which is potentially hazardous and explosive, herein, a new route to ε-caprolactone was developed in which molecule oxygen was employed as the terminal oxidant. The commercial available N-hydroxyphthalimide and ammonium cerium nitrate were used as the key catalysts for the increased yield of ε-caprolactone. For instance, the selectivity of ε-caprolactone was obtained 92 % with 85 % conversion of cyclohexanone which was comparable to the strategies using highly concentrated hydrogen peroxide. The sacrificed alcohols were transformed into corresponding ketones which were also valuable chemicals. Furthermore, the efficiency of the alcohols was achieved to unprecedented 52 %. The Baeyer-Villiger oxidation of various other cycloalkanones was also examined. The substituent group effect on the efficiency of sacrificed alcohols was investigated in which weak electron-donating substituent induced nearly quantitative yield of ε-caprolactone. The reaction mechanism was studied with the help of electron paramagnetic resonance which indicated the existence of a radical pathway.
Du, Renfeng,Li, Haoran,Wang, Yongtao,Yao, Jia,Yuan, Haoran,Zhao, Chenxuan
(2020/04/27)

Photo-induced phosphorus radical involved semipinacol rearrangement reaction: Highly synthesis of γ-oxo-phosphonates
Hydroxyphosphoric acids display the unique biological activities, and they have some attractive prospects as clinical drug moleculars. Herein, a new approach for the synthesis of γ-oxo-phosphonates (the precursor of hydroxyphosphoric acid) has been established through the semipinacol rearrangement tactic involved the photo-induced phosphorus radical process. Most important, this transformation is avoid of the external oxidants, and occurs very well under the sunlight irradiation, meanwhile the γ-oxo-phosphonate was easily derivatized to obtain γ-hydroxyphosphoric acid, thus highlights the synthesis value of this method.
Wang, Chunhai,Huang, Xiaoling,Liu, Xueting,Gao, Suqian,Zhao, Bin,Yang, Shangdong
p. 677 - 680
(2019/08/27)

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)

Ruthenium-Catalyzed Dehydrogenation of Alcohols with Carbodiimide via a Hydrogen Transfer Mechanism
Ruthenium-catalyzed oxidative dehydrogenation of alcohols using carbodiimide as an efficient hydrogen acceptor has been developed. The protocol exhibits wide substrate scope with good to excellent yields. The results of the kinetic analysis indicated that the reaction mechanism includes the hydrogen transfer process and that the addition of carbodiimide is essential for the reaction system, and the resulting amidine also could react as a hydrogen acceptor.
Sueki, Shunsuke,Matsuyama, Mizuki,Watanabe, Azumi,Kanemaki, Arata,Katakawa, Kazuaki,Anada, Masahiro
p. 4878 - 4885
(2020/06/02)

Nature-mimic fabricated polydopamine/MIL-53(Fe): Efficient visible-light responsive photocatalysts for the selective oxidation of alcohols
Polydopamine/MIL-53(Fe) (PDA/MIL-53(Fe)) nanocomposite photocatalysts were synthesized with PDA (PDA = polydopamine) and MIL-53(Fe) using a nature-mimicking method. The structures, morphologies, optical properties and thermal stabilities of all the synthesized materials were characterized using a series of methods. In particular, the separation efficiency of photogenerated charge significantly increased after the incorporation of PDA into MIL-53(Fe), which resulted in an elevated photocatalytic activity of PDA/MIL-53(Fe) compared with the control groups. The PDA/MIL-53(Fe) nanocomposite could accelerate the conversion of primary or secondary alcohols into the corresponding aldehydes or ketones with a high specificity by direct hole-involving oxidation under visible-light irradiation and room temperature. The catalysts could be cycled at least three times without a significant decrease in the catalytic activity and this result showed the excellent recyclability and stability of the catalysts.
Meng, Shuangyan,Zeng, Wei,Wang, Mingming,Niu, Litong,Hu, Shaoping,Su, Bitao,Yang, Yaoxia,Yang, Zhiwang,Xue, Qunji
p. 2102 - 2110
(2020/02/13)

Fabrication of a new heterogeneous tungstate-based on the amino-functionalized metal-organic framework as an efficient catalyst towards sonochemical oxidation of alcohols under green condition
Ultrasonic-assisted reactions, as a green technique, are often more efficient compared to those traditional protocols. To this end, the selective and solvent-free oxidation of aromatic alcohols to the corresponding aldehydes and ketones were investigated in the presence of Co-ABDC/W at room temperature under ultrasonic irradiation conditions for the first time in this paper. The structure, particle size, thermal stability, and morphology of the fabricated heterogeneous catalyst and the products were characterized by FT-IR, EDS, FE-SEM, XRD, TGA, and GC analyses. In this regard, immobilization of tungstate had a significant effect on thermal stability (around 450 °C for 40percent weight loss) and catalytic performance. Moreover, the efficiency of two different oxidation methods, including ultrasound irradiations and reflux, were comparatively investigated by GC spectrometry. Obtained sonoxidation results presented higher conversions ranging (84 to 100percent) than reflux condition via shorter reaction times. The influences of the reaction parameters, such as hydrogen peroxide concentration, and catalyst loading, were also investigated. The proposed method offers several advantages, such as excellent conversions, selective oxidations, environmentally-benign procedure, short reaction times, and easy workup. Notably, this is the first report that focuses on using amino-functionalized MOFs with ultrasonic irradiation for selective oxidation reactions.
Aghajani, Zahra,Najafi, Gholam Reza,Sabaghi, Maryam
(2020/09/01)

Method for preparing symmetric diarylketone through catalytic oxidative carbonylation
The invention discloses a method for preparing symmetric diarylketone of a formula (I) as shown in the description. The method comprises the following steps: mixing arylboronic acid (II) (Ar-B(OH)2 (II)), a palladium catalyst, a promoter and an organic solvent in a reactor, introducing air and CO having a volume ratio of (7-19):1, reacting under the conditions of a pressure of 1-6 atm and a temperature of 30-80 DEG C for 8-16 hours, and performing after-treatment on the reaction solution, thereby obtaining the product symmetric diarylketone. According to the method disclosed by the invention,the air directly serves as an oxidizing agent to replace the O2 to be applied to oxidative carbonylation of the arylboronic acid, and the ratio of the air to CO is beyond an explosion limit. Therefore, the catalytic system is safe and economic. The palladium catalyst is small in dosage and simple in separation and can be recycled for several times. The method disclosed by the invention is mild inreaction condition, excellent in substrate suitability and high in yield.
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Paragraph 0023; 0024; 0025; 0026; 0029

(2019/03/08)

A Deoximation Method for Deprotection of Ketones and Aldhydes Using a Graphene-Oxide-Based Co-catalysts System
The deoximation of a wide range of ketoximes and aldoximes to their corresponding carbonyl compounds with high yields has been achieved using graphene oxide (GO) and sodium nitrite (NaNO2) as highly efficient catalysts and air as the green oxidant under mild conditions. The mechanism of deprotection and recycling use of catalyst were revealed in deep experiment. The carboxylic acid groups on the GO were essential for high catalytic activity. (Figure presented.).
Tong, Qiaolin,Liu, Yang,Gao, Xuezhi,Fan, Zhanfang,Liu, Tianfu,Li, Bo,Su, Dangsheng,Wang, Qinghe,Cheng, Maosheng
supporting information
p. 3137 - 3145
(2019/05/01)

Iron-Enabled Utilization of Air as the Terminal Oxidant Leading to Aerobic Oxidative Deoximation by Organoselenium Catalysis
In contrast to conventional organoselenium-catalyzed oxidation reactions that require peroxide oxidants such as hydrogen peroxide, in this work we found that, addition of a low loading of iron (II) could enable the successful utilization of air as the terminal oxidant in organoselenium-catalyzed oxidative deoximation reaction of ketoximes. This led to a new mild and relatively green aerobic oxidative deoximation method. Control reactions and X-ray photoelectron spectroscopy (XPS) analysis suggest that iron is crucial in the catalytic cycle, working to prohibit the deactivation of selenium catalyst through an iron-catalyzed aerobic oxidation of low valent selenium species by air to the active high valent selenium species. Since air can be utilized as the terminal oxidant, this work may contribute to the advance of organoselenium catalysis. (Figure presented.).
Chen, Chao,Zhang, Xu,Cao, Hongen,Wang, Fang,Yu, Lei,Xu, Qing
p. 603 - 610
(2018/12/14)

Cercosporin-bioinspired selective photooxidation reactions under mild conditions
The development of an efficient system for selective oxidation of organic compounds to generate more valuable compounds with molecular oxygen is a significant challenge in industrial chemistry. Bioinspired by the ability of naturally occurring perylenequinonoid pigments (PQPs) to generate reactive oxygen species (ROS) upon photoirradiation, here we report that cercosporin, one of the perylenequinonoid pigments, can function as a cost-effective and environmentally friendly photocatalyst for a wide range of selective oxidations, including benzylic C-H bonds to carbonyls, amines to aldehydes, and sulfides to sulfoxides. All of the representative reactions proceeded smoothly with high efficiency under mild conditions. Owing to the use of inexpensive metal-free visible light-driven photocatalyst produced from microbial fermentation with cheap glucose as the starting material and the ease of handling, we expect that this developed method will be particularly attractive for many more applications in synthetic transformation.
Li, Jia,Bao, Wenhao,Tang, Zhaocheng,Guo, Baodang,Zhang, Shiwei,Liu, Haili,Huang, Shuping,Zhang, Yan,Rao, Yijian
supporting information
p. 6073 - 6081
(2019/11/20)

Photo-nickel dual catalytic benzoylation of aryl bromides
The dual catalytic arylation of aromatic aldehydes by aryl bromides using UV-irradiation and a nickel catalyst is reported. The reaction product serves as a photocatalyst and a hydrogen atom transfer agent for this transformation.
Schirmer, Tobias Emanuel,Wimmer, Alexander,Weinzierl, Florian Wolfgang Clemens,K?nig, Burkhard
supporting information
p. 10796 - 10799
(2019/09/13)

A facile approach to constructing Pd@PCN-Se nano-composite catalysts for selective alcohol oxidation reactions
By using selenium as the structure-directing agent, Se-incorporated polymeric carbon nitride (PCN-Se) was prepared for the first time and could be used as a superexcellent support for Pd nanoparticles (NPs). A trace amount of Se dopant (0.01 wt%) was found to play an unexpectedly vital role in increasing the materials' surface area and total mesoporous volume by 4.5 and 2 times respectively, so the Pd@PCN-Se catalyst might contain even more active sites than its simple PCN and Pd@PCN counterparts, and a strong interaction between Se(0) and Pd(ii) was also built-in, affording a dramatically improved catalytic activity as well as good recycling stability in selective catalytic alcohol oxidation reactions.
Cao, Kuanhong,Deng, Xin,Chen, Tian,Zhang, Qitao,Yu, Lei
supporting information
p. 10918 - 10923
(2019/05/17)

Pyridiniumporphyrazinato oxo-vanadium tribromomethanide as a new source of Br+ catalyst for the chemo and homoselective oxidation of sulfides and benzylic alcohols
The present study describes the design and synthesis of novel nano N-bromo porphyrazin (N-bromo tetra-2,3-pyridiniumporphyrazinato oxo-vanadium tribromomethanide [VO(TPPABr)] CBr3) as an efficient, recyclable and thermal stable heterogeneous catalyst for chemo and homoselective oxidation of sulfides to sulfoxides and benzyl alcohols to benzaldehydes. This ecofriendly heterogeneous catalyst was fully characterized by FT-IR spectra, UV–Vis spectra, X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), and thermal gravimetric analysis (TGA), energy-dispersive X-ray spectroscopy (EDX) and elemental analysis (CHN). The synthesized catalyst exhibited a high-performance and considerable reusability.
Safaiee, Maliheh,Moeinimehr, Mahtab,Zolfigol, Mohammad Ali
p. 138 - 150
(2019/06/17)

Pd-NHC catalysed Carbonylative Suzuki coupling reaction and its application towards the synthesis of biologically active 3-aroylquinolin-4 (1H)-one and acridone scaffolds
We have unfolded a convenient and mild protocol for the synthesis of diaryl ketones via Pd- NHC catalysed carbonylative Suzuki coupling reaction. Notably, this method offers advantages like no use of toxic CO gas, shorter reaction time, high yield, and broad substrate scope. Several sensitive functional groups (like-COMe, -COOMe, -F, -Cl, -Br, -NH2, -CN) are well tolerated in this reaction. In addition, we have also demonstrated a new efficient route for the synthesis of biologically active and pharmaceutically important 2-substituted 3-Aroylquinolin-4(1H)-ones and acridone scaffolds.
Ghosh, Prasanjit,Ganguly, Bhaskar,Das, Sajal
(2018/03/01)

Palladium-Catalyzed Carbonylative Homocoupling of Aryl Iodides for the Synthesis of Symmetrical Diaryl Ketones with Formic Acid
A convenient method for the palladium-catalyzed carbonylative homocoupling of aryl iodides was developed. With formic acid as the CO source, various symmetrical diaryl ketones were synthesized in moderate to good yield in the presence of a palladium catalyst.
Wu, Fu-Peng,Peng, Jin-Bao,Qi, Xinxin,Wu, Xiao-Feng
p. 173 - 177
(2017/11/27)

Pd-Catalyzed Suzuki–Miyaura Cross-Coupling of Arylboronic Acids and α-Iminonitriles through C–CN Bond Activation
A Pd-catalyzed Suzuki–Miyaura cross-coupling reaction between arylboronic acids and α-iminonitriles has been developed. The reaction proceeds through selective activation of the C–CN bond, tolerates a wide range of substituents, and delivers the versatile ketone products in moderate to excellent yields.
Liu, Kui,Tao, Shou-Wei,Qian, Chun,Zhu, Yong-Ming
supporting information
p. 4769 - 4775
(2018/09/06)

MeZnOMe-mediated reaction of aldehydes with Grignard reagents: A glance into nucleophilic addition/Oppenauer oxidation pathway
A novel organozincate of RMgX ?MeZnOMe ?LiCl type, formed in situ via transmetalation of Grignard reagent RMgBr ?LiCl with MeZnOMe, is shown to be an excellent organometallic species in the nucleophilic addition/Oppenauer oxidation of aldehydes to generate aromatic ketones in high yield. This transformation allows quick access to structurally diverse aryl, heteroaryl, benzyl and alkyl ketones with broad substrate scope and excellent functional group tolerance.
Fu, Ying,Ma, Xian-Zhen,Shi, Chun-Zhao,Shen, Tong,Du, Zhengyin
(2018/07/31)

Nickel-Catalyzed Molybdenum-Promoted Carbonylative Synthesis of Benzophenones
A nickel-catalyzed molybdenum-promoted carbonylative coupling reaction for the synthesis of benzophenones from aryl iodides has been developed. Various substituted diaryl ketones were synthesized in moderate to excellent yields under CO-gas-free conditions. A synergetic effect of both nickel and molybdenum has been observed, which is also responsible for the success of this transformation.
Peng, Jin-Bao,Wu, Fu-Peng,Li, Da,Qi, Xinxin,Ying, Jun,Wu, Xiao-Feng
p. 6788 - 6792
(2018/06/04)

Revealing the Structure and Reactivity of the Active Species in the FeCl2-TBHP System: Case Study on Alkene Oxidation
A mechanism involving a quintet ferryl [FeIV=O] species has been disclosed for the oxidation of alkene under the FeCl2-TBHP system. Both theoretical and experimental results suggested that the quintet ferryl species [FeIV=O] was produced by the reaction of FeCl2 with TBHP. A Mulliken atomic spin density distribution on [FeIV=O] showed that the O site has strong radical character and could easily react with alkene to form a carbon radical intermediate. This radical could be further oxidized by TBHP to lead to the C=C bond cleavage of alkene.
Huang, Zhiliang,Qi, Xiaotian,Lee, Jyh-Fu,Lei, Aiwen
supporting information
p. 1635 - 1640
(2018/06/11)

Sodium copper chlorophyllin catalyzed chemoselective oxidation of benzylic alcohols and diarylmethanes in water
We report the highly efficient and chemoselective oxidation of benzylic alcohols catalyzed by sodium copper chlorophyllin in water, producing corresponding arylcarbonyl compounds. Importantly, the catalytic system exhibits a wide substrate scope and high functional group tolerance. Moreover, secondary alcohols and even diarylmethanes were smoothly oxidized to the desired aryl ketones with excellent yields.
Liu, Shi-juan,Zhang, Miao,Lu, Rong,Li, Xiu-ying,Che, Guang-bo
(2018/08/17)

CO2-Catalyzed oxidation of benzylic and allylic alcohols with DMSO
CO2-catalyzed transition-metal-free oxidation of alcohols has been achieved. Earlier, several methodologies have been explored for alcohol oxidations based on transition-metal catalysts. However, owing to the cheaper price, easy separation and nontoxicity, transition-metal-free systems are in high demand to the pharmaceutical industries. For this reason, various primary and secondary alcohols have been selectively oxidized to the corresponding carbonyl compounds using CO2 as a catalyst in the presence of different functional groups such as nitrile, nitro, aldehyde, ester, halogen, ether, and so on. At the end, transition-metal-free syntheses of pharmaceuticals have also been achieved. Finally, the role of CO2 has been investigated in detail, and the mechanism is proposed on the basis of experiments and DFT calculations.
Riemer, Daniel,Mandaviya, Bhavdip,Schilling, Waldemar,G?tz, Anne Charlotte,Kühl, Torben,Finger, Markus,Das, Shoubhik
p. 3030 - 3034
(2018/04/14)

Kinetic studies on tetrabutylammonium bromochromate oxidation of some mono-and di-substituted benzhydrols
The oxidation of 12 mono- and di-substituted benzhydrols (BH) by tetrabutylammonium bromochromate (TBABC) have been studied in aqueous acetic acid medium. Absence of any effect of added acrylonitrile on the reaction discounts the possibility of a one-electron oxidation, leading to the formation of free radicals. The tetrabutylammonium bromochromate oxidation of 12 mono- and di-substituted benzhydrols complies with the isokinetic relationship and Hammett relationship. The overall mechanism is proposed to involve a cyclic concerted symmetrical transition state leading to the product.
Hemalatha,Asghar, Basim H.,Mansoor, S Sheik
p. 821 - 826
(2018/03/13)

Compounds and methods for the reduction of halogenated hydrocarbons
The present application relates to methods for the reduction of halogenated hydrocarbons using compounds of Formula (I): wherein the reduction of the halogenated compounds is carried out, for example, under ambient conditions without the need for a transition metal containing co-factor. The present application also relates to methods of recovering precious metals using compounds of Formula (I) that are absorbed onto a support material.
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Page/Page column 20-21

(2017/12/27)

Organoselenium-Catalyzed Oxidative C=C Bond Cleavage: A Relatively Green Oxidation of Alkenes into Carbonyl Compounds with Hydrogen Peroxide
A relatively green oxidative C=C bond cleavage of alkenes was achieved by organoselenium-catalyzed alkene oxidation reaction in ethanol with hydrogen peroxide, affording carbonyl compounds under relatively mild conditions. It is a new reaction style for the organoselenium-catalyzed oxidation of alkenes and largely contributes to the growing field of organoselenium catalysis.
Wang, Tingting,Jing, Xiaobi,Chen, Chao,Yu, Lei
p. 9342 - 9349
(2017/09/23)

A kind of alkali to promote self-oxidation of diaryl alkane preparation diarylketones method (by machine translation)
The invention discloses a kind of alkali to promote self-oxidation of diaryl alkane preparation diarylketones method. The method is that the diaryl paraffins compound is dissolved in an organic solvent in the drying of, the addition of a base, in the 25 - 80o C reaction under air or oxygen atmosphere for 0.5 - 5 hours, to obtain diarylketones; said two aryl paraffins compound and alkali molar ratio of 1:1 - 1:3. The method overcomes the need in the prior art strong acid or expensive metal reagent or a strong oxidizing agent and the like, has the following advantages: 1) to oxygen as the oxidizing agent, avoids the use of strong or expensive chemical oxidizing agent; 2) transition metal-free catalyst, avoids the heavy metal ion in the product; 3) the process is simple, low cost, wide range of the substrate, friendly to the environment. The synthesis method disclosed in this invention in the preparation of diarylketones industrialization of the play an important role in the production. (by machine translation)
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Paragraph 0019

(2017/08/28)

A gassing by olefin method
The invention provides a simple synthetic method for synthesizing a ketone from an olefin, and relates to the field of the synthetic technology of carbonyl compounds. The method includes the step that ceric ammonium nitrate serves as a catalyst, oxygen serves as an oxidizing agent, and the disubstituted terminal olefin is subjected to catalytic oxidation to prepare the carbonyl compound. Compared with a traditional method, the method is environmentally friendly and high in yield, reaction conditions are moderate, no ligand is used, the usage amount of the catalyst is small, a substrate is wide in application range, and the method is the simple synthetic method for synthesizing ketones.
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Paragraph 0016; 0037-0041

(2017/07/06)

Regeneration of aldehydes and ketones by the oxidation of oximes using potassium permanganate-graphite with grinding under solvent-free conditions
A facile and efficient procedure for the oxidative cleavage of oximes to their parent aldehydes and ketones by grinding with potassium permanganate-graphite at room temperature under solvent-free conditions in the yields between 80 and 94% is described. All reactions are complete in 5 min.
Zhu, Li-Yun,Song, Lin-zhen,Chen, Wei,Gao, Yong-sheng,Zhang, Chunmiao,Wang, Jiaping,Qian, Jun-qing
p. 1326 - 1329
(2017/12/26)

Green and Practical Oxidative Deoximation of Oximes to Ketones or Aldehydes with Hydrogen Peroxide/Air by Organoselenium Catalysis
Organoselenium-catalyzed oxidative deoximations afforded ketones and aldehydes under mild conditions. The reactions employ hydrogen peroxide and air as clean oxidants and lead to a waste-free and metal-free deprotection protocol for carbonyl protection strategies as well as the green synthesis of ketones and aldehydes. The mechanisms of this interesting organoselenium-catalyzed reaction have been investigated by control experiments as well as the selenium 77 nuclear magnetic resonance (77Se NMR) tests. This novel reaction largely expands the application scope of organoselenium catalysis. (Figure presented.).
Jing, Xiaobi,Yuan, Dandan,Yu, Lei
p. 1194 - 1201
(2017/04/13)