1139-60-2Relevant academic research and scientific papers
An efficient Fe2O3/HY catalyst for Friedel-Crafts acylation of m-xylene with benzoyl chloride
Mu, Manman,Chen, Ligong,Liu, Yunlong,Fang, Wangwang,Li, Yang
, p. 36951 - 36958 (2014)
Iron oxide supported on HY zeolite was prepared and exhibited excellent catalytic performance in the acylation of m-xylene with benzoyl chloride. It was characterized by XRD, BET, XPS, NH3-TPD and Py-IR. The obtained results indicated that the catalytic activity of Fe2O3/HY is enhanced with the increase of Lewis acidic sites. Furthermore, the reaction parameters, including load of Fe2O3, temperature, molar ratio and the dose of catalyst, were optimized. Thus the acylation proceeds effectively to afford 2,4-dimethylphenylacetophenone in 94.1% yield under optimum conditions. Finally, the catalyst was examined for the acylations of a series of arenes, all of the alkyl substituted benzenes were transformed to the corresponding products in satisfactory yields while the acylation of chlorobenzene was sluggish. The catalyst was easily separated from the reaction mixture and reused for five runs without appreciable loss of catalytic activity. the Partner Organisations 2014.
Experimental and DFT study on the indium-mediated synthesis of benzophenones via arylstannanes
Lo Fiego, Marcos J.,Dorn, Viviana B.,Badajoz, Mercedes A.,Lockhart, Mara T.,Chopa, Alicia B.
, p. 49079 - 49085 (2014)
Experimental results of the solvent-free, indium-promoted reaction of aroyl chlorides with arylstannanes showed a narrow scope; its efficiency depends both on the extent of methylation in the latter and on the nature, number and position of the substituents in the former. With the purpose of explaining experimental results, a theoretical analysis with DFT methods was performed for a set of selected cases. This journal is
Friedel-crafts benzoylation of alkylbenzenes with brazoic anhydride catalyzed by solid superacids
Nakamura, Hideo,Arata, Kazushi
, p. 1893 - 1896 (2004)
The liquid-solid phase benzoylation of mono-alkylbenzenes with methyl, ethyl, propyl, and butyl groups and xylenes was carried out with benzoic anhydride at 100-110°C over solid superacids: SO4/ZrO 2, WO3/ZrO2, and SO4/ HfO 2. The reactivity ratio obtained by the competitive method of reaction over WO3/ZrO2 was 1 to 4.6 for toluene to p-xylene and 1.1:10:1 among o-, m-, and p-xylenes, respectively. Although the SO4/ZrO2 catalyst gave high yields of 92 and 97% for toluene and ethylbenzene in a 3:7 distribution of o- and p-isomers, respectively, low yields were observed with propyl and butylbenzenes over the catalyst: that is, 5 and 2% for propylbenzene and isopropylbenzene, 14% for isobutylbenzene, and trace yields for butylbenzene, s-butylbenzene, and t-butylbenzene, respectively. The usual Friedel-Crafts benzoylation using AlCl3 was examined in the present alkylbenzenes in order to confirm the low reactivity of both propyl and butylbenzenes. The results were similar to those with the SO4/ZrO2 catalyst; that is, the yields at 0°C for 1 h were 37, 21, 6, 1, 0, 3, and 2% for toluene, ethylbenzene, propylbenzene, isopropylbenzene, butylbenzene, s-butylbenzene, and t-butylbenzene, respectively, showing an unexpected result where there was no distinction between homogeneous and heterogeneous conditions.
Sterically Hindered Ketones via Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Amides by N-C(O) Activation
Liu, Chengwei,Lalancette, Roger,Szostak, Roman,Szostak, Michal
, p. 7976 - 7981 (2019/10/10)
Herein, we report a new protocol for the synthesis of sterically hindered ketones that proceeds via palladium-catalyzed Suzuki-Miyaura cross-coupling of unconventional amide electrophiles by selective N-C(O) activation. Mechanistic studies demonstrate that steric bulk on the amide has a major impact, which is opposite to the traditional Suzuki-Miyaura cross-coupling of sterically hindered aryl halides. Structural and computational studies provide insight into ground-state distortion of sterically hindered amides and show that ortho-substitution alleviates the N-C(O) bond twist.
Ketone Synthesis by a Nickel-Catalyzed Dehydrogenative Cross-Coupling of Primary Alcohols
Verheyen, Thomas,Van Turnhout, Lars,Vandavasi, Jaya Kishore,Isbrandt, Eric S.,De Borggraeve, Wim M.,Newman, Stephen G.
supporting information, (2019/05/08)
An intermolecular coupling of primary alcohols and organotriflates has been developed to provide ketones by the action of a Ni(0) catalyst. This oxidative transformation is proposed to occur by the union of three distinct catalytic cycles. Two competitive oxidation processes generate aldehyde in situ via hydrogen transfer oxidation or (pseudo)dehalogenation pathways. As aldehyde forms, a Ni-catalyzed carbonyl-Heck process enables formation of the key carbon-carbon bond. The utility of this rare alcohol to ketone transformation is demonstrated through the synthesis of diverse complex and bioactive molecules.
Ketone Synthesis by a Nickel-Catalyzed Dehydrogenative Cross-Coupling of Primary Alcohols
Verheyen, Thomas,Van Turnhout, Lars,Vandavasi, Jaya Kishore,Isbrandt, Eric S.,De Borggraeve, Wim M.,Newman, Stephen G.
supporting information, p. 6869 - 6874 (2019/05/10)
An intermolecular coupling of primary alcohols and organotriflates has been developed to provide ketones by the action of a Ni(0) catalyst. This oxidative transformation is proposed to occur by the union of three distinct catalytic cycles. Two competitive oxidation processes generate aldehyde in situ via hydrogen transfer oxidation or (pseudo)dehalogenation pathways. As aldehyde forms, a Ni-catalyzed carbonyl-Heck process enables formation of the key carbon-carbon bond. The utility of this rare alcohol to ketone transformation is demonstrated through the synthesis of diverse complex and bioactive molecules.
Ligand-free Palladium-Catalyzed Carbonylative Suzuki Coupling of Aryl Iodides in Aqueous CH3CN with Sub-stoichiometric Amount of Mo(CO)6 as CO Source
Sun, Nan,Sun, Qingxia,Zhao, Wei,Jin, Liqun,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
, p. 2117 - 2123 (2019/03/28)
A new method for the synthesis of diaryl and heterodiaryl ketones has been established based on the palladium-catalyzed carbonylative Suzuki coupling approach with sub-stoichiometric Mo(CO)6 as CO source. Using 0.5 mol% of Pd(TFA)2 as catalyst, 0.5 equivalent of Mo(CO)6 as solid carbonyl reagent and 3 equivalent of K3PO4 as base, a wide range of functionalized (hetero)aryl iodides and (hetero)aryl boronic acids could smoothly proceed the carbonylative cross-coupling reaction in aqueous CH3CN at 50 °C, affording the corresponding ketones in good to excellent yields. The newly developed method was easy to operate under mild conditions with high efficiency. (Figure presented.).
Palladium-Catalyzed Ligand-Free Decarboxylative Coupling of α- Oxocarboxylic Acid with Aryl Diazonium Tetrafluoroborate: An Access to Unsymmetrical Diaryl Ketones
Panja, Subir,Maity, Pintu,Ranu, Brindaban C.
, p. 12609 - 12618 (2018/10/20)
Diaryl ketones are of much importance in organic synthesis as versatile intermediates and in industry for their useful properties. A mild and efficient palladium-catalyzed traditional ligand-free decarboxylative coupling of aryl α-keto carboxylic acid with aryl diazonium fluoroborate has been developed. A series of unsymmetrical diaryl ketones has been synthesized in moderate to good yields using this procedure. A radical pathway involving the acyl radical has been suggested.
Carbonylative Suzuki cross-coupling reaction catalyzed by bimetallic Pd-Pt nanodendrites under ambient CO pressure
Wang, Zheng-Jun,Wang, Xue-Yan,Wang, Xia,Liang, Zhi-Wu,Xu, Xinhua
, p. 10 - 14 (2017/07/22)
Pd-catalyzed reactions between aryl boronic acids and aryl halides have undergone rapid development since the pioneering work of Suzuki and co-workers in 1979. In this paper, we described a high-efficient and cost-effective bimetallic Pd-Pt nanodendrites catalyst based on a ligand-free strategy to synthesize diaryl ketones via CO direct insertion to boronic acids and aryl halides. A variety of aryl boronic acids and aryl halides were investigated, which showed great functional group tolerance and versatile aryl ketone products in high yield.
Palladium-Catalyzed Denitrogenative Synthesis of Aryl Ketones from Arylhydrazines and Nitriles Using O2 as Sole Oxidant
Wang, Xu,Huang, Yubing,Xu, Yanli,Tang, Xiaodong,Wu, Wanqing,Jiang, Huanfeng
, p. 2211 - 2218 (2017/02/26)
An efficient and simple palladium-catalyzed approach for the synthesis of aryl ketones from low-cost nitriles and arylhydrazines using molecular oxygen (O2) as sole oxidant via C-N bond cleavage is reported. Various aryl ketones were synthesized in moderate to good yields under mild conditions. A possible mechanism involving the PdII/Pd0 catalytic cycle process is depicted, and a cationic palladium intermediate was detected by ESI-MS.
