- Iodine Promoted Conversion of Esters to Nitriles and Ketones under Metal-Free Conditions
-
We report a novel strategy to prepare valuable nitriles and ketones through the conversion of esters under metal-free conditions. By using the I2/PCl3 system, various substrates including aliphatic and aromatic esters could react with acetonitrile and arenes to afford the desired products in good to excellent yields. This method is compatible with a number of functional groups and provides a simple and practical approach for the synthesis of nitrile compounds and aryl ketones.
- Xiao, Jing,Guo, Fengzhe,Li, Yinfeng,Li, Fangshao,Li, Qiang,Tang, Zi-Long
-
p. 2028 - 2035
(2021/02/03)
-
- Carbon-wrapped Fe-Ni bimetallic nanoparticle-catalyzed Friedel-Crafts acylation for green synthesis of aromatic ketones
-
Developing highly efficient and durable eco-friendly heterogeneous catalysts for the Friedel-Crafts acylation (FCA) reaction has been a long-term and significant target, yet remains a great challenge. Herein, a series of Fe-Ni alloy nanoparticles (NPs) encapsulated inside N-doped carbon spheres (FexNi1?x@NC) was rationally fabricated by pyrolyzing the Fe-Ni bimetallic metal-organic frameworks (BMOFs-FexNi1?x) to this end. Various characterization results demonstrated that FeNi alloy NPs (25 nm) covered by a thin carbon shell (5 nm) were uniformly distributed throughout the entire carbon-based composite. A number of oxidized metal species (Fe3+, Ni2+) are present on the surface of the inner bimetallic core, which should be the main source of catalytically active centers of the carbon-wrapped metal NP catalysts. The composition-optimized Fe0.8Ni0.2@NC with relatively higher positive surface charges exhibited the highest catalytic activity and excellent stability for the acylation of aromatic compounds with acyl chlorides. The density functional theory calculations revealed that the catalytic activity of the FexNi1?x@NC catalysts could arise from the electron transfer,i.e., from the outermost layer of the carbon shell to the inner positively charged Fe-based metal NPs, which can lead to a positive charge distribution (by acting as weak Lewis acid sites) on the external surface of the carbon-encapsulated metal NP catalysts. In this case, the external carbon shell can function as ‘chainmail’ to transfer the Lewis acidity (positive charge), and also to protect the inner metal core from the destructive reaction environment, thus resulting in the formation of highly efficient and durable FCA catalysts.
- Bao, Shouxin,Hu, Dianwen,Jia, Mingjun,Lei, Zhenyu,Liu, Jingyao,Song, Xiaojing,Sun, Hao,Zhang, Hao,Zhang, Wenxiang,Zhao, Chen
-
p. 7943 - 7954
(2021/12/27)
-
- Oxidative Cleavage of Alkenes by O2with a Non-Heme Manganese Catalyst
-
The oxidative cleavage of C═C double bonds with molecular oxygen to produce carbonyl compounds is an important transformation in chemical and pharmaceutical synthesis. In nature, enzymes containing the first-row transition metals, particularly heme and non-heme iron-dependent enzymes, readily activate O2 and oxidatively cleave C═C bonds with exquisite precision under ambient conditions. The reaction remains challenging for synthetic chemists, however. There are only a small number of known synthetic metal catalysts that allow for the oxidative cleavage of alkenes at an atmospheric pressure of O2, with very few known to catalyze the cleavage of nonactivated alkenes. In this work, we describe a light-driven, Mn-catalyzed protocol for the selective oxidation of alkenes to carbonyls under 1 atm of O2. For the first time, aromatic as well as various nonactivated aliphatic alkenes could be oxidized to afford ketones and aldehydes under clean, mild conditions with a first row, biorelevant metal catalyst. Moreover, the protocol shows a very good functional group tolerance. Mechanistic investigation suggests that Mn-oxo species, including an asymmetric, mixed-valent bis(μ-oxo)-Mn(III,IV) complex, are involved in the oxidation, and the solvent methanol participates in O2 activation that leads to the formation of the oxo species.
- Bennett, Elliot L.,Brookfield, Adam,Guan, Renpeng,Huang, Zhiliang,Mcinnes, Eric J. L.,Robertson, Craig M.,Shanmugam, Muralidharan,Xiao, Jianliang
-
supporting information
p. 10005 - 10013
(2021/07/19)
-
- 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.
- -
-
Paragraph 0078-0083
(2021/06/22)
-
- Acylboronates in polarity-reversed generation of acyl palladium(II) intermediates
-
We report a catalytic cross-coupling process between aryl (pseudo)halides and boron-based acyl anion equivalents. This mode of acylboronate reactivity represents polarity reversal, which is supported by the observation of tetracoordinated boronate and acyl palladium(II) species by 11B, 31P NMR, and mass spectrometry. A broad scope of aliphatic and aromatic acylboronates has been examined, as well as a variety of aryl (pseudo)halides.
- Trofimova, Alina,Holownia, Aleksandra,Tien, Chieh-Hung,?irvinskas, Martynas J.,Yudin, Andrei K.
-
supporting information
p. 3294 - 3299
(2021/05/07)
-
- Tunable aryl imidazolium recyclable ionic liquid with dual br?nsted-lewis acid as green catalyst for friedel-crafts acylation and thioesterification
-
Unique tunable aryl imidazolium ionic liquids successfully catalyzed Friedel-Crafts acylation and thioesterification in sealed tubes. These reactions can form a C-C bond and a C-S bond with high atom economy. Ionic liquids exhibited high activity and catalyzed essential reactions with good to excellent yields while retaining their catalytic activities for recycling.
- Chen, Wen-Tin,Chou, Shih-Huan,Ho, Wen-Yueh,Hung, Ming-Wei,Lin, Michelle,Lin, Wesley,Lin, Yi-Jyun,Luo, Shun-Yuan,Reddy, Daggula Mallikarjuna,Thul, Mayur,Wu, Hsin-Ru,Wu, Yao-Peng
-
-
- Sterically Hindered Ketones via Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Amides by N-C(O) Activation
-
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.
- Liu, Chengwei,Lalancette, Roger,Szostak, Roman,Szostak, Michal
-
supporting information
p. 7976 - 7981
(2019/10/10)
-
- Chemoselective Synthesis of Aryl Ketones from Amides and Grignard Reagents via C(O)-N Bond Cleavage under Catalyst-Free Conditions
-
Conversion of a wide range of N-Boc amides to aryl ketones was achieved with Grignard reagents via chemoselective C(O)-N bond cleavage. The reactions proceeded under catalyst-free conditions with different aryl, alkyl, and alkynyl Grignard reagents. α-Ketoamide was successfully converted to aryl diketones, while α,β-unsaturated amide underwent 1,4-addition followed by C(O)-N bond cleavage to provide diaryl propiophenones. N-Boc amides displayed higher reactivity than Weinreb amides with Grignard reagents. A broad substrate scope, excellent yields, and quick conversion are important features of this methodology.
- Sureshbabu, Popuri,Azeez, Sadaf,Muniyappan, Nalluchamy,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
-
p. 11823 - 11838
(2019/10/02)
-
- Transition-metal-free carbonylation of aryl halides with arylboronic acids by utilizing stoichiometric CHCl3 as the carbon monoxide-precursor
-
Under transition-metal-free conditions, carbonylative Suzuki couplings of aryl halides with arylboronic acid using stoichiometric CHCl3 as the carbonyl source has been developed. The simple, efficient, and environmentally benign method was successfully applied to the synthesis of Fenofibric acid, naphthyl phenstatin, and carbon-13 labeled biaryl ketone.
- Xu, Fangning,Li, Dan,Han, Wei
-
supporting information
p. 2911 - 2915
(2019/06/18)
-
- Transition-Metal-Free Carbonylative Suzuki-Miyaura Reactions of Aryl Iodides with Arylboronic Acids Using N-Formylsaccharin as CO Surrogate
-
Unprecedented, high yielding, transition-metal-free carbonylative Suzuki-Miyaura reactions of aryl iodides with arylboronic acids using N-formylsaccharin as CO surrogate have been developed. Notably, this general protocol was adapted to the synthesis of the triglyceride and cholesterol regulator drug, fenofibrate, and carbon-13 labeled biaryl ketone. (Figure presented.).
- Yu, Dezhong,Xu, Fangning,Li, Dan,Han, Wei
-
supporting information
p. 3102 - 3107
(2019/05/21)
-
- A convenient and practical heterogeneous palladium-catalyzed carbonylative Suzuki coupling of aryl iodides with formic acid as carbon monoxide source
-
A practical heterogeneous palladium-catalyzed carbonylative Suzuki coupling of aryl iodides with arylboronic acids under carbon monoxide gas-free conditions has been developed using a bidentate phosphino-functionalized magnetic nanoparticle-immobilized palladium(II) complex as catalyst. Formic acid was utilized as the carbon monoxide source with dicyclohexylcarbodiimide as the activator, and a wide variety of biaryl ketones were generated in moderate to high yields. The new heterogeneous palladium catalyst can be prepared via a simple procedure and can easily be separated from a reaction mixture by simply applying an external magnet and recycled up to 10 times without any loss of activity.
- You, Shengyong,Yan, Chenyu,Zhang, Rongli,Cai, Mingzhong
-
-
- P -Selective (sp2)-C-H functionalization for an acylation/alkylation reaction using organic photoredox catalysis
-
p-Selective (sp2)-C-H functionalization of electron rich arenes has been achieved for acylation and alkylation reactions, respectively, with acyl/alkylselenides by organic photoredox catalysis involving an interesting mechanistic pathway.
- Pandey, Ganesh,Tiwari, Sandip Kumar,Singh, Bhawana,Vanka, Kumar,Jain, Shailja
-
p. 12337 - 12340
(2017/11/20)
-
- Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of N-Mesylamides by N-C Cleavage: Electronic Effect of the Mesyl Group
-
A general Pd-catalyzed Suzuki-Miyaura cross-coupling of N-mesylamides with arylboronic acids by selective N-C cleavage has been developed. The presented results represent the first example of a transition-metal-catalyzed cross-coupling of amides activated by an atom-economic, cheap, and benign mesyl group. The reaction delivers arylated products featuring a range of useful functional groups by chemoselective cleavage of the amide N-C bond with high efficiency. Both the scope and the origin of high selectivity are discussed. A beneficial effect of the N-mesyl substituent on the bond activation in acyclic amides is presented.
- Liu, Chengwei,Liu, Yongmei,Liu, Ruzhang,Lalancette, Roger,Szostak, Roman,Szostak, Michal
-
supporting information
p. 1434 - 1437
(2017/03/23)
-
- An efficient combination of Zr-MOF and microwave irradiation in catalytic Lewis acid Friedel-Crafts benzoylation
-
A zirconium-based metal-organic framework, an effective heterogeneous catalyst, has been developed for the Friedel-Crafts benzoylation of aromatic compounds under microwave irradiation. Constructed by a Zr(iv) cluster and a linker 1,4-bis(2-[4-carboxyphenyl]ethynyl)benzene (H2CPEB), the MOF, possessing large pores and high chemical stability, was appropriate for the enhancement of Lewis acid activity under microwave irradiation. The reaction studies demonstrated that the material could give high yields for a few minutes and maintain its reactivity and structure over several cycles.
- Doan, Tan L. H.,Dao, Thong Q.,Tran, Hai N.,Tran, Phuong H.,Le, Thach N.
-
supporting information
p. 7875 - 7880
(2016/05/24)
-
- An efficient and green method for regio- and chemo-selective Friedel-Crafts acylations using a deep eutectic solvent ([CholineCl][ZnCl2]3)
-
[CholineCl][ZnCl2]3, a deep eutectic solvent between choline chloride and ZnCl2, has been used as a dual function catalyst and green solvent for the Friedel-Crafts acylation of aromatic compounds instead of using the moisture-sensitive Lewis acids and volatile organic solvents. The reactions are performed with high yields under microwave irradiation with short reaction times for the synthesis of ketones. Interestingly, indole derivatives are regioselectively acylated in the 3-position under mild conditions with high yields without NH protection. Three new ketone products are synthesized. [CholineCl][ZnCl2]3 is easily synthesized from choline chloride and zinc chloride at a low cost, with easy purification and environmentally benign compounds. [CholineCl][ZnCl2]3 can be reused up to five times without loss of catalytic activity, making it ideal in industrial processes.
- Tran, Phuong Hoang,Nguyen, Hai Truong,Hansen, Poul Erik,Le, Thach Ngoc
-
p. 37031 - 37038
(2016/05/24)
-
- Erbium trifluoromethanesulfonate catalyzed Friedel-Crafts acylation using aromatic carboxylic acids as acylating agents under monomode-microwave irradiation
-
Erbium trifluoromethanesulfonate is found to be a good catalyst for the Friedel-Crafts acylation of arenes containing electron-donating substituents using aromatic carboxylic acids as the acylating agents under microwave irradiation. An effective, rapid and waste-free method allows the preparation of a wide range of aryl ketones in good yields and in short reaction times with minimum amounts of waste.
- Tran, Phuong Hoang,Hansen, Poul Erik,Nguyen, Hai Truong,Le, Thach Ngoc
-
p. 612 - 618
(2015/02/19)
-
- An efficient Fe2O3/HY catalyst for Friedel-Crafts acylation of m-xylene with benzoyl chloride
-
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.
- Mu, Manman,Chen, Ligong,Liu, Yunlong,Fang, Wangwang,Li, Yang
-
p. 36951 - 36958
(2014/12/11)
-
- Improvement of the Friedel-Crafts benzoylation by using bismuth trifluoromethanesulfonate in 1-butyl-3-methylimidazolium trifluoromethanesulfonate ionic liquid under microwave irradiation
-
Bismuth trifluoromethanesulfonate (bismuth triflate) catalyzed the Friedel-Crafts benzoylation of activated aromatic compounds when dissolved in 1-butyl-3-methylimidazolium trifluoromethanesulfonate ([BMIM]OTf) ionic liquid. Immobilization of bismuth triflate (5 mol %) in [BMIM]OTf allowed the synthesis of aryl ketones in good to excellent yields with short reaction times under microwave irradiation. This catalytic system was easily recovered and reused several times without any significant loss of the activity.
- Hoangtran, Phuong,Bichle Do, Ngoc,Ngocle, Thach
-
p. 205 - 208
(2014/01/06)
-
- Microwave-assisted facile and rapid friedel-crafts benzoylation of arenes catalyzed by bismuth trifluoromethanesulfonate
-
The catalytic activity of metal triflates was investigated in Friedel-Crafts benzoylation under microwave irradiation. Friedel-Crafts benzoylation with benzoyl chloride of a variety of arenes containing electron-rich and electron-poor rings using bismuth triflate under microwave irradiation is described. This method allows the preparation of aryl ketones under solventless conditions in good to excellent yields and short reaction time. Bismuth triflate was easily recovered and reused five times without significant loss of the catalytic activity.
- Tran, Phuong Hoang,Hansen, Poul Erik,Pham, Thuy Thanh,Huynh, Vy Thanh,Huynh, Vy Hieu,Thi Tran, Thao Du,Huynh, Thanh Van,Le, Thach Ngoc
-
p. 2921 - 2929
(2014/10/15)
-
- Synthesis, structural characterization, and catalytic evaluation of phosphinoferrocene ligands bearing extended urea-amide substituents
-
New phosphinoferrocene ligands bearing extended polar amidourea pendants with the general formula Ph2PfcCONHCH2CH 2NHCONR2 (1; R2 = H2 (b), H/Et (c), Me2 (d), H/Ph (e)) and their model bis-amide Ph 2PfcCONHCH2CH2NHCOCH3 (1a) were prepared in good yields by amidation of 1′-(diphenylphosphino)ferrocene-1- carboxylic acid (Hdpf) with the appropriate amines in the presence of peptide coupling reagents. These ferrocene-based phosphinoureas were further employed as ligands in palladium(II) complexes with η3-allyl and NC-chelating supporting ligands: viz., [PdCl(η3-C 3H5)(1-κP)] (5a-e) and [PdCl(LNC)(1- κP)] (6a-e; LNC = [2-(dimethylamino-κN)methyl]phenyl- κC1). Both the free ligands and their Pd(II) complexes were characterized by spectroscopic methods (multinuclear NMR, IR, and MS) and by elemental analysis. The molecular structures of 1b·CH3OH, 1c, 5b,c, 6a, and two additional model complexes, [PdCl(η3-C 3H5)(Hdpf-κP)] (5f) and [PdCl(η3- C3H5)(Ph2PfcCONH2-κP)] (5g), were determined by single-crystal X-ray diffraction analysis. All Pd(II) complexes were evaluated as catalysts in the cross-coupling of boronic acids and acyl halides to give ketones in a toluene/water biphasic mixture. Extensive reaction studies with compound 5e, which not only exerts good catalytic activity but is also readily accessible in a defined crystalline form, demonstrated efficient coupling reactivity for unsaturated substrates such as (substituted) benzeneboronic acids and benzoyl chlorides. The results also revealed that reaction difficulties encountered with less reactive substrates (e.g., insoluble aromatic boronic acids and all saturated aliphatic boronic acids) can be avoided by properly selecting the reaction partners, for example through transposition of substituents between reaction partners. Three representative benzophenones (4-fluoro-, 4-nitro-, and 4,4′-dinitrobenzophenone) were structurally characterized by single-crystal X-ray crystallography.
- Solarova, Hana,Cisarova, Ivana,Stepnicka, Petr
-
p. 4131 - 4147
(2014/10/15)
-
- Catalytic Friedel-Crafts acylation: Magnetic nanopowder CuFe 2O4 as an efficient and magnetically separable catalyst
-
Catalytic regioselective Friedel-Crafts acylation of an array of anisoles/arenes with various acid chlorides using 5-20 mol % of magnetic nanopowder CuFe2O4 is reported. Unlike the conventional Friedel-Crafts reactions, which are catalyzed by moisture sensitive homogeneous catalysts/promoters, the nanopowder CuFe2O4 catalyst is moisture insensitive and the product/ketone-catalyst isolation is easily achieved using the magnetic properties of CuFe2O4.
- Parella, Ramarao,Naveen,Kumar, Amit,Babu, Srinivasarao Arulananda
-
p. 1738 - 1742
(2013/03/28)
-
- Catalysis studies of macroreticular polystyrene cation-exchange resin with terminal perfluoroalkanesulfonic acids
-
Macroreticular p-(ω-sulfonic-perfluoroalkylated) polystyrene (FPS) resin with the advantages of both sulfonic polystyrene (such as macroreticular Amberlyst-15) and perfluoroalkanesulfonic resin (such as superacidic Nafion NR50) has exhibited excellent catalytic selectivity and activity in cyclization of pseudoionone and condensation of indole. In this paper, FPS was characterized by XPS, nitrogen sorption technique, FESEM and Hammett indicator method, and employed as the solid acid catalyst in the esterification, acylation and alkylation reactions. The FPS resin showed better activity than commercial solid acid catalysts (Amberlyst-15 and Nafion NR50) owing to its high surface area and strong acidity close to superacidity.
- Lin, Zhenghuan,Guan, Chuanjin,Huang, Limei,Wang, Wen,Ling, Qidan,Zhao, Chengxue
-
p. 261 - 266
(2013/07/27)
-
- Ultrasound-assisted synthesis of benzophenones by Stille cross-coupling reactions. Optimization via experimental design
-
A series of diaryl ketones have been synthesized in moderate to excellent yields through the selective cross-coupling reaction of benzoyl chlorides with arylstannanes using a sonochemical variation of the Stille coupling. Ultrasound significantly enhances this useful organometallic transformation affording the desired products in higher yields and shorter reaction times than conventional reactions. The scope of the protocol has been explored with a selection of arylstannanes and different aroyl chlorides as reaction partners. Remarkably, no by-products resulting from homo-coupling could be detected. The ultrasound-promoted cross-coupling reaction was optimized through experimental design.
- Luong, Martín,Domini, Claudia E.,Silbestri, Gustavo F.,Chopa, Alicia B.
-
-
- Friedel-crafts acylation of arenes with carboxylic acids using polystyrene-supported aluminum triflate
-
Cross-linked polystyrene-supported aluminum triflate (Ps-Al(OTf) 3) has been shown to be a mild, efficient, and chemoselective heterogeneous Lewis acid catalyst for the acylation of aromatic compounds. The catalyst can be easily prepared from cheap starting materials, is stable (as a bench top catalyst) and is reusable.
- Boroujeni, Kaveh Parvanak,Parvanak, Kamran
-
experimental part
p. 155 - 163
(2012/01/02)
-
- Pd(II)-Catalyzed decarboxylative cross-coupling of potassium aryltrifluoroborates with α-oxocarboxylic acids at room temperature
-
A novel Pd-catalyzed decarboxylative cross-coupling of potassium aryltrifluoroborates with R-oxocarboxylic acids is performed at room temperature. This reaction provides an efficient access to aryl ketones under mild conditions.
- Li, Mingzong,Wang, Cong,Ge, Haibo
-
supporting information; experimental part
p. 2062 - 2064
(2011/06/19)
-
- Friedel-Crafts acylation of arenes with carboxylic acids using silica gel supported AlCl3
-
Aromatic compounds react smoothly with carboxylic acids in the presence of silica gel supported aluminium trichloride to afford the corresponding ketones with high regioselectivity in high to excellent yields. The catalyst is stable (as a bench top catalyst) and can be easily recovered and reused without appreciable change in its efficiency. tuebitak.
- Parvanak Boroujeni, Kaveh
-
experimental part
p. 621 - 630
(2010/11/04)
-
- Silica gel supported AlCl3 catalyzed Friedel-Crafts acylation of aromatic compounds
-
Silica gel supported aluminium trichloride (SiO2-AlCl3) has been shown to be a mild, efficient, and chemoselective heterogeneous Lewis acid catalyst for the acylation of aromatic compounds with acid chlorides. The catalyst can be reused up to five times after simple washing with ether and is stable (as a bench top catalyst).
- Boroujeni, Kaveh Parvanak
-
experimental part
p. 1395 - 1398
(2011/10/09)
-
- Polystyrene supported Al(OTf)3: An environmentally friendly heterogeneous catalyst for Friedel-Crafts acylation of aromatic compounds
-
Stable and non-hygroscopic polystyrene supported aluminium triflate (Ps-Al(OTf)3), which is prepared easily from cheap and commercially available compounds was found to be an environmentally friendly heterogeneous catalyst for Friedel-Crafts acylation of arenes using acid chlorides in the absence of solvent under mild reaction conditions. The catalyst can be reused up to five times after simple washing with dichloromethane.
- Boroujeni, Kaveh Parvanak
-
experimental part
p. 3156 - 3158
(2012/05/20)
-
- Simple and efficient procedure for the friedel-crafts acylation of aromatic compounds with carboxylic acids in the presence of P2O5/AL2O3 under heterogeneous conditions
-
An efficient and chemoselective method for the Friedel-Crafts acylation of aromatic compounds using P2O5/Al2O3 and carboxylic acids. Both aromatic and aliphatic carboxylic acids reacted easily to afford the corresponding aromatic ketones in good yields.
- Hajipour, Abdol R.,Zarei, Amin,Khazdooz, Leila,Ruoho, Arnold E.
-
experimental part
p. 2702 - 2722
(2009/12/06)
-
- Friedel-Crafts acylation of aromatic compounds with carboxylic acids in the presence of P2O5/SiO2 under heterogeneous conditions
-
A convenient and efficient procedure for the Friedel-Crafts acylation of aromatic compounds with carboxylic acids in the presence of P2O5/SiO2 is described. Both aromatic and aliphatic carboxylic acids reacted easily to afford the corresponding aromatic ketones. The use of non-toxic and inexpensive materials, simple and clean work-up, short reaction times and good yields of the products are the advantages of this method.
- Zarei, Amin,Hajipour, Abdol R.,Khazdooz, Leila
-
scheme or table
p. 6715 - 6719
(2009/04/07)
-
- An efficient method for aromatic Friedel-Crafts acylation reactions
-
Friedel-Crafts acylation of aromatic compounds was carried out using FeCl3-based ionic liquid. This liquid serves as an efficient media as well as a Lewis acid catalyst. The significant advantages of this methodology are excellent yields, short reaction times, mild reaction conditions, environmentally friendly method, simple work-up procedure, low cost, and easy preparation and handling of the catalyst. Copyright
- Khodaei, Mohammad Mehdi,Bahrami, Kiumars,Shahbazi, Fomeida
-
p. 844 - 845
(2008/12/22)
-
- Tf2O as a rapid and efficient promoter for the dehydrative Friedel-Crafts acylation of aromatic compounds with carboxylic acids
-
The Friedel-Crafts acylation of aromatic compounds with carboxylic acids was investigated in the presence of Tf2O. The reaction was carried out efficiently and very rapidly under mild reaction conditions without the need of any catalyst.
- Khodaei, Mohammd Mehdi,Alizadeh, Abdolhamid,Nazari, Ehsan
-
p. 4199 - 4202
(2008/02/05)
-
- Highly selective catalytic Friedel-Crafts acylation and sulfonylation of activated aromatic compounds using indium metal
-
The Friedel-Crafts acylation of activated benzenes with various aromatic and aliphatic acid chlorides was studied in the presence of indium metal. The reaction was accomplished in high isolated yields under solvent or solvent-less conditions. The method is also applicable for preparing diaryl sulfones from aromatic compounds and aryl sulfonyl chlorides.
- Jang, Doo Ok,Moon, Kyung Soo,Cho, Dae Hyan,Kim, Joong-Gon
-
p. 6063 - 6066
(2007/10/03)
-
- Boron carbide as an effective Friedel-Crafts type catalyst
-
The compound boron carbide, B4C, is an effective catalyst for the alkylation and acylation of aromatics to produce polybenzyls, ketones, esters and alkyl benzenes. The catalyst boron carbide is also effective in conducting intramolecular Freidel-Crafts type reactions to produce cyclic ketones.
- -
-
Page/Page column 2
(2008/06/13)
-
- Hf[N(SO2C8F17)2] 4-catalyzed Friedel-Crafts acylation in a fluorous biphase system
-
In a fluorous biphase system, Hf[N(SO2C8F 17)2]4 complex (1 mol %) catalyzes Friedel-Crafts acylation of aromatic compounds such as anisole, toluene and chlorobenzene, and the corresponding aromatic ketones are obtained in satisfactory to high yields. The catalyst is selectively soluble in lower fluorous phase and can be easily recovered by simple phase separation. Furthermore, the catalyst can be reused without decrease of activity in most cases.
- Hao, Xiuhua,Yoshida, Akihiro,Nishikido, Joji
-
p. 2697 - 2700
(2007/10/03)
-
- ACYLATION OF AROMATIC COMPOUNDS
-
This invention particularly relates to a process for the acylation of aromatic compounds by an acylating agent for preparing corresponding acylated aromatic compounds, using a solid catalyst.
- -
-
Page/Page column 5; 6
(2008/06/13)
-
- A rapid, solvent-free, ligandless and mild method for preparing aromatic ketones from acyl chlorides and arylboronic acids via a Suzuki-Miyaura type of coupling reaction
-
Aromatic ketones were synthesized via a palladium catalyzed cross-coupling reaction of boronic acids with acyl chlorides in the presence of Na 2CO3 at room temperature under solvent-free conditions. The ligand-free and mild reaction conditions, highly rapid reaction rate and good to excellent yields are important features of this method.
- Bandgar,Patil
-
p. 7627 - 7630
(2007/10/03)
-
- Niobium pentachloride-silver perchlorate as an efficient catalyst in the Friedel-Crafts acylation and Sakurai-Hosomi reaction of acetals
-
Friedel-Crafts acylation catalyzed by niobium pentachloride with silver salt is described. Aromatic compounds with Ac2O or Bz2O were smoothly converted into the corresponding ketones in good to excellent yields. This system was also applied to the Sakurai-Hosomi reaction using acetals. The reaction proceeded quite rapidly to give the desired products in excellent yields.
- Arai, Shigeru,Sudo, Yukinori,Nishida, Atsushi
-
p. 4639 - 4642
(2007/10/03)
-
- The Friedel-Crafts acylation of aromatic compounds with carboxylic acids by the combined use of perfluoroalkanoic anhydride and bismuth or scandium triflate
-
Aromatic ketones were synthesized by solventless Friedel-Crafts acylation of anisole, mesitylene, xylenes, and toluene with acetic acid and benzoic acid in the presence of trifluoroacetic anhydride by use of bismuth or scandium triflate at 30°C. Toluene, benzene, and even deactivated substrate such as chlorobenzene were benzoylated by the combined use of heptafluorobutyric anhydride and bismuth triflate at 75-100°C. The catalyst could be easily recovered and reused repeatedly for the reaction.
- Matsushita, Yoh-Ichi,Sugamoto, Kazuhiro,Matsui, Takanao
-
p. 4723 - 4727
(2007/10/03)
-
- Aluminum dodecatungstophosphate (AlPW12O40) as a non-hygroscopic Lewis acid catalyst for the efficient Friedel-Crafts acylation of aromatic compounds under solvent-less conditions
-
Stable and non-hygroscopic aluminum dodecatungstophosphate (AlPW 12O40), which is prepared easily from cheap and commercially available compounds was found to be an effective catalyst for Friedel-Crafts acylation reactions using carboxylic acids, acetic anhydride and benzoyl chloride in the absence of solvent under mild reaction conditions.
- Firouzabadi, Habib,Iranpoor, Nasser,Nowrouzi, Farhad
-
p. 10843 - 10850
(2007/10/03)
-
- Synthesis of Diaryl Ketones Catalyzed by Al2O 3-ZrO2/S2O82- Solid Superacid
-
The acylation of a variety of aromatic compounds with benzoyl chloride or its derivatives and catalytic amounts of Al2O3-ZrO 2/S2O82- solid superacid affords the corresponding diaryl ketones in good to excellent yields 75-93% at appropriate temperature.
- Jin, Tong-Shou,Yang, Mi-Na,Feng, Guo-Liang,Li, Tong-Shuang
-
p. 479 - 485
(2007/10/03)
-
- High-Throughput Synthesis of Alkylbenzophenones with Indium Triflate in the Absence of Solvents Using Microwave
-
A series of alkylbenzophenones were rapidly and efficiently prepared from alkylbenzenes and benzoyl chlorides by Friedel-Crafts acylation catalyzed with indium triflate under solvent-free conditions by microwave heating.
- Koshima, Hideko,Kubota, Masashi
-
p. 3983 - 3988
(2007/10/03)
-
- BiCl3-catalyzed Friedel-Crafts acylation reactions: Bismuth(III) oxychloride as a water insensitive and recyclable procatalyst
-
The Friedel-Crafts acylation of activated and polycyclic aromatics is efficiently catalyzed by bismuth(III) chloride which is generated in situ from bismuth(III) oxychloride, a water insensitive and eco-friendly material. Bismuth(III) oxychloride is easily recovered in near quantitative yields after an aqueous work-up.
- Répichet, Sigrid,Le Roux, Christophe,Roques, Nicolas,Dubac, Jacques
-
p. 2037 - 2040
(2007/10/03)
-
- Acylation of aromatic compounds using moisture insensitive InCl3 impregnated mesoporous Si-MCM-41 catalyst
-
Acylation of aromatic compounds (benzene, toluene, p-xylene, mesitylene, anisole, naphthalene, methylnaphthalene and methoxynaphthalene) by an acyl chloride (benzoyl chloride, phenylacetyl chloride, propionyl chloride or butyryl chloride) in high yield, in a short reaction period (3 h), even in the presence of moisture in the aromatic substrate or solvent (dichloroethane), can be accomplished at low temperature (80±1°C) using an InCl3 impregnated Si-MCM-41 catalyst in low catalyst concentration.
- Choudhary, Vasant R.,Jana, Suman K.,Patil, Nilesh S.
-
p. 1105 - 1107
(2007/10/03)
-
- Acylation of aromatic compounds using moisture insensitive mesoporous Si-MCM-41 supported Ga2O3 catalyst
-
Mesoporous Si-MCM-41 supported Ga2O3 is a highly active catalyst for the acylation of aromatic compounds with different acyl chlorides. Moreover, this catalyst is not deactivated by water and hence does not require moisture-free reaction conditions.
- Choudhary, Vasant R.,Jana, Suman K.
-
p. 2843 - 2848
(2007/10/03)
-
- A new method for the synthesis of ketones: The palladium-catalyzed cross-coupling of acid chlorides with arylboronic acids
-
The cross-coupling reaction of acid chlorides with arylboronic acids, using catalytic amounts of Pd(PPh3)4 and five equivalents Cs2CO3, under anhydrous conditions provides a new method for the synthesis of ketones in good to moderate yields.
- Haddach, Mustapha,McCarthy, James R.
-
p. 3109 - 3112
(2007/10/03)
-
- Experimental measurements of low-Frequency intermolecular host-guest dynamics
-
A direct temporal measurement of the internal motion of a host-guest bimolecular complex is reported. Time-resolved polarization spectroscopy is used to monitor the motion of a guest chromophore, anthracene-1,3-dicarboxylate, bound to a bis(guanidinium) h
- Sukharevsky, Alexander P.,Read, Ian,Linton, Brian,Hamilton, Andrew D.,Waldeck, David H.
-
p. 5394 - 5403
(2007/10/03)
-
- Graphite as an effective catalyst for Friedel-Crafts acylation
-
Graphite is found to promote Friedel-Crafts acylation of aromatic compounds such as anisole, toluene and o-xylene with acyl halides to give the corresponding acylated products in high yields.
- Kodomari, Mitsuo,Suzuki, Yoshitada,Yoshida, Kouji
-
p. 1567 - 1568
(2007/10/03)
-
- Electrocycloreversion of benzocyclobutenols promoted by photoinduced electron transfer
-
Benzocyclobutenols 1 undergo electron-transfer induced electrocycloreversion to generate o-quinodimethane intermediates E-4 and Z-4, which then tautomerize to benzophenones 2. Evidence for the intermediates is provided by the trapping experiments and the laser flash photolysis experiments.
- Takahashi, Yasutake,Miyamoto, Kazuya,Sakai, Kazuhiro,Ikeda, Hiroshi,Miyashi, Tsutomu,Ito, Yoshikatsu,Tabohashi, Ken
-
p. 5547 - 5550
(2007/10/03)
-