- Imidazolium-Based Ionic Network as a Robust Heterogeneous Catalyst in Synthesis of Phenacyl Derivatives
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A new imidazolium-based poly(ionic liquid) has been synthesized and used as a robust heterogeneous catalyst for the preparation of phenacyl derivatives by an SN2 reaction of different phenacyl bromides with a broad range of nucleophiles. The products are obtained in high yields under mild conditions. The catalyst can be recycled efficiently.
- Kakesh,Sayyahi,Badri,Tahanpesar
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- Efficient α-iodination of carbonyl compounds under solvent-free conditions using microwave irradiation
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Direct conversion of carbonyl compounds into α-iodocarbonyl compounds has been successfully achieved under solvent-free microwave irradiation conditions using N-iodosuccinimide and p-toluenesulfonic acid.
- Lee, Jong Chan,Bae, Yong Hun
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- Facile aerobic photo-oxidative synthesis of phenacyl iodides and bromides from styrenes using I2 or aqueous HBr
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We report a useful method for facile synthesis of phenacyl iodides and bromides from styrene derivatives by aerobic photo-oxidation using I2 or 48% aqueous HBr in the presence of water. Georg Thieme Verlag Stuttgart - New York.
- Nobuta, Tomoya,Hirashima, Shin-Ichi,Tada, Norihiro,Miura, Tsuyoshi,Itoh, Akichika
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- One-pot synthesis of α-iodoketones from alcohols using ammonium iodide and Oxone in water
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A novel protocol for the synthesis of α-iodoketones from alcohols has been developed. Using water as the reaction medium, ammonium iodide and Oxone was proven to be an efficient reagent system for this reaction and afforded the corresponding α-iodoketones in moderate to good yields. The generality of this reaction was demonstrated with various secondary alcohols such as benzylic alcohols and aliphatic alcohols (acyclic and cyclic).
- Reddy, Marri Mahender,Swamy, Peraka,Naresh, Mameda,Srujana, Kodumuri,Durgaiah, Chevella,Rao, Tumula Venkateshwar,Narender, Nama
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- Integration of aqueous biphasic with magnetically recyclable systems: Polyethylene glycol-grafted Fe3O4 nanoparticles catalyzed phenacyl synthesis in water
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The present work trends to define an efficient phenacyl catalytic synthesis method employing a new nano-magnetite-supported organocatalyst. Polyethylene glycol (PEG) was bonded successfully onto silica coated ferrite and the resultant nanoparticles (PEG@SiO2@Fe3O4) characterized by fourier transform infrared spectroscopy (FT-IR), atomic force microscopy (AFM), thermal gravimetric analysis (TGA), vibrating sample magnetometry (VSM), energy dispersive X-ray analysis (EDAX) and X-ray diffraction (XRD) that exhibited a good catalytic activity in the reaction. The nanoparticles could be easily separated from the reaction mixture by an external magnet and reused in seven reaction cycles without significant loss of activity.
- Amini, Atefeh,Sayyahi, Soheil,Saghanezhad, Seyyed Jafar,Taheri, Narges
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- Facile synthesis of phenacyl iodides from styrenes under visible light irradiation with fluorescent lamps
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Phenacyl iodides were easily synthesized from styrenes with iodine under irradiation of visible light from a fluorescent lamp.
- Nakayama, Hiroki,Itoh, Akichika
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- An efficient method for synthesis of phenacyl derivatives under homogeneous phase transfer catalyst condition in aqueous media
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In this letter, a mild and efficient procedure for synthesis of phenacyl derivatives under homogenous catalysis in the presence of tetrabutylammonium bromide in aqueous media is described. The nucleophilic substitution reactions were performed under ecofriendly conditions and gave the corresponding products in high yields and short reaction times.
- Sayyahi, Soheil,Saghanezhad, Jafar
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- Carbon-13 NMR Spectra of Some 4-Substituted Phenacyl Chlorides and Iodides
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The 13C NMR signals for some 4-substituted phenacyl chlorides and iodides were assigned.The carbonyl carbons exhibit upfield shifts compared with those of the corresponding 4-substituted acethophenones; in the chlorinated derivatives a downfield shift is observed for the α-methylene carbons, while a reverse effect occurs in the iodinated compounds.The chemical shifts of the aromatic ring carbons are in close agreement with those calculated using substituent chemical shifts.KEY WORDS 13C NMR 4-substituted pheacyl chlorides and iodides
- Olivato, Paulo Roberto,Guerrero, Sandra Alvarez,Rittner, Roberto
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- A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions
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A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions has been developed. In the presence of PhI(OAc)2 as promoter and under ambient conditions, the reactions of styrenes and triiodomethane undergo the transformation smoothly to deliver the corresponding α-iodoketones without additional photocatalyst in good yields under sunlight irradiation. Meanwhile, the reactions of styrenes with tribromomethane and trichloromethane generate the desired α-bromoketones and α-chloroketones in high yields by using Ru(bpy)3Cl2 as a photocatalyst under blue LED (450–455 nm) irradiation.
- Wang, Zhihui,Wang, Lei,Wang, Zhiming,Li, Pinhua,Zhang, Yicheng
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supporting information
p. 429 - 432
(2020/02/29)
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- A simple method for the synthesis of furfuryl ketones and furylacetic acid derivatives
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A simple preparative method has been developed for the synthesis of aryl(furfuryl) ketones, amides, and furylacetic acid esters, based on radical alkylation of furan derivatives at the α-position with O-ethyl(phenacyl)xanthogenates and phenacyl iodides in the presence of Fenton's reagent (H2O2/FeSO4·7H2O) in DMSO. The range of applicability and mechanisms for the formation of major and side products have been considered.
- Chalikidi, Petrakis N.,Nevolina, Tatyana A.,Uchuskin, Maxim G.,Abaev, Vladimir T.,Butin, Alexander V.
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p. 621 - 629
(2015/10/12)
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- Aerobic oxidative α-iodination of carbonyl compounds using molecular iodine activated by a nitrate-based catalytic system
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The novel reaction system comprising air/NH4NO3(cat.)/I2/H2SO4(cat.)is introduced as a simple, safe, cheap, efficient, and regioselective mediator for direct aerobic oxidative α-iodination of aryl, heteroaryl, alkyl, and cycloalkyl methyl ketones. The reaction system enabled the moderate to quantitative regioselective iodination of a large range of different methyl ketone derivatives including those bearing oxidizable heteroatom (S, N) substituents. Several activated aromatic compounds were also efficiently and selectively iodinated. The practical applicability of the presented reaction system was shown on 20 mmol scale under ambient pressure and 100% conversion of substrate was achieved.
- Prebil, Rok,Stavber, Stojan
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supporting information
p. 5643 - 5647
(2014/12/11)
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- I2-DMSO catalyzed synthesis of 1,2,2-triarylethanones via dual C-H activation of aryl methyl ketones
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An I2-DMSO promoted domino protocol was developed for the synthesis of 1,2,2-triarylethanones from readily available aromatic methyl ketones and methoxybenzenes. The 1,2,2-triarylethanones are important precursors for the synthesis of Tamoxifen
- Raghavender Reddy,Nageswara Rao,Ramakrishna,Meshram
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supporting information
p. 1898 - 1901
(2014/03/21)
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- Metal-free in situ sp3, sp2, and sp C-H functionalization and oxidative cross coupling with benzamidines hydrochloride: A promising approach for the synthesis of α-ketoimides
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A new metal-free tandem protocol for the synthesis of α-ketoimides via sp3, sp2, and sp C-H functionalization followed by oxidative cross coupling with benzamidines hydrochloride using catalytic iodine with TBHP in DMSO has been developed. A wide range of functional group tolerance, an inexpensive catalyst, operational simplicity and good to excellent yields of the products are the striking features of this method.
- Kalmode, Hanuman P.,Vadagaonkar, Kamlesh S.,Chaskar, Atul C.
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p. 60316 - 60326
(2015/02/19)
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- Design and synthesis of 2-acylbenzothiazoles via in situ cross-trapping strategy from benzothiazoles with aryl ketones
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An I2/KOH synergistically promoted direct ring-opening aroylation of benzothiazoles with aryl ketones has been discovered. Aryl ketones were seen to act as carbonyl sources to construct 2-acylbenzothiazoles. This reaction could provide an example for the convergent integration of self-labor domino sequences based on an in situ cross-trapping strategy.
- Gao, Qinghe,Wu, Xia,Jia, Fengcheng,Liu, Meicai,Zhu, Yanping,Cai, Qun,Wu, Anxin
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p. 2792 - 2797
(2013/04/24)
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- Target-oriented synthesis: Miscellaneous synthetic routes to access 1,4-enediones through the coupling of 1,3-dicarbonyl compounds with multiform substrates
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Target-oriented synthetic protocol was presented for the synthesis of 1,4-enediones. The approach can efficiently construct 1,4-enediones through different reaction pathways from multiform substrates α-halo aromatic ketones, 2-hydroxy-aromatic ketones and methyl carbinols. In this reaction, CuI was found to be the most efficient catalyst. Multiform substrates were also found to perform well to afford the products in a one-pot fashion.
- Zhu, Yan-Ping,Cai, Qun,Gao, Qing-He,Jia, Feng-Cheng,Liu, Mei-Cai,Gao, Meng,Wu, An-Xin
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supporting information
p. 6392 - 6398
(2013/07/25)
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- Oxidative iodination of carbonyl compounds using ammonium iodide and oxone
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A simple, efficient, mild, and regioselective method for oxyiodination of carbonyl compounds has been reported by using NH4I as the source of iodine and Oxone as an oxidant. Various carbonyl compounds such as aralkyl ketones, aliphatic ketones (acyclic and cyclic), and β-keto esters proceeded to the respective α-monoiodinated products in moderate to excellent yields. Unsymmetrical aliphatic ketones reacted smoothly yielding a mixture of 1-iodo and 3-iodo ketones with the predominant formation of 1-iodoproduct.
- Marri, Mahender Reddy,MacHarla, Arun Kumar,Peraka, Swamy,Nama, Narender
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supporting information; experimental part
p. 6554 - 6559
(2012/01/02)
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- Highly efficient and clean method for direct α-iodination of aromatic ketones
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Under neutral reaction conditions, aromatic ketones were transformed into the corresponding α-iodo ketones in high yields by the combination of copper(II) oxide and iodine. The reaction mechanism showed that copper(II) oxide played multiple roles through random self-sorting. Georg Thieme Verlag Stuttgart.
- Yin, Guodong,Gao, Meng,She, Nengfang,Hu, Shengli,Wu, Anxin,Pan, Yuanjiang
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p. 3113 - 3116
(2008/09/16)
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- Efficient microwave induced direct α-halogenation of carbonyl compounds
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A novel and direct method for the synthesis of α-halocarbonyl compounds using sequential treatment of carbonyl compounds with [hydroxy(tosyloxy)iodo]benzene followed by magnesium halides under solvent-free microwave irradiation conditions is described.
- Lee, Jong Chan,Park, Jin Young,Yoon, So Young,Bae, Yong Hun,Lee, Seung Jun
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p. 191 - 193
(2007/10/03)
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- Preparation of Aromatic Iodoacetyl Derivatives by Direct Iodination with a Potassium Iodide-Potassium Iodate-Sulfuric Acid System
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The reaction of aromatic acetyl derivatives with potassium iodide and potassium iodate in acetic acid in the presence of sulfuric acid at room temperature gave iodoacetyl derivatives in good yields.
- Okamoto, Tsuyoshi,Kakinami, Takaaki,Nishimura, Tetsuo,Irwan-Hermawan,Kajigaeshi, Shoji
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p. 1731 - 1733
(2007/10/02)
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- Oxidative Assistance in the Conversion of α-Iodoketones to α-Ketols
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Treatment with bis(trifluoroacetoxy)iodobenzene (2) followed by hydrolysis converted five phenacyl iodides 1a-e to phenacyl alcohols 8a-d, 9 but failed to convert exo-3-iodonorbornan-2-one (10) and 2-iodocyclohexanone (11) to α-ketols.Iodinations by proposed intermediate trifluoroacetoxy iodide (5) were assumed to explain the formation of p-diiodobenzene (7) and 2-hydroxy-1-(3'-iodo-4'-methoxyphenyl)ethanone (9).
- Boyer, Joseph H.,Natesh, Anbazhagan
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p. 980 - 981
(2007/10/02)
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- Reactions of Aryl Ketones and Coumarins with Iodine(III) Tris(trifluoroacetate)
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The reaction of acetophenones with iodine(III) tris(trifluoroacetate) yields 3'- and/or 2-iodo derivatives, depending upon the substituent on the aromatic ring and the reaction conditions.The reaction was examinedby changing the molar ratio of acetophenone versus the reagent, reaction temperature, and solvent.In similar reactions flavanones and coumarins gave iodo derivatives in which iodine is incorporated at various positions orientated by the oxygen functions. 1,2-Diphenylethanone yields 2-hydroxy-2-(2-iodophenyl)-1-phenylethanone and 1-(2-iodophenyl)-2-phenylethanedione.The reactions of other aromatic ketones such as 9-xanthenone, 9-fluorenone, and anthrone also give iodo derivatives in moderate to good yields.The mechanisms for the iodination at the α-carbon to the carbonyl group have been discussed.
- Fukuyama, Norihiro,Nishino, Hiroshi,Kurosawa, Kazu
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p. 4363 - 4368
(2007/10/02)
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- General Base Catalysis in Acetophenone-Iodine Reactions: Hammett-Bronsted Correlations
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The rate constants and activation parameters for the reaction of carboxylate buffer catalysed iodination of acetophenones have been measured in aqueous methanol.The reaction is zero order in iodine and first order each in ketone and catalyst.The catalytic
- Satyanarayana, N.,Sundaram, E. V.
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p. 747 - 752
(2007/10/02)
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- Kinetics of Iodination of Ketones by N-Iodosuccinimide in Acid Medium
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The kinetics of iodination of some ketones by N-iodosuccinimide (NIS) has been studied in aq. acetic acid medium in the presence of HClO4.The reaction is acid-catalysed exhibiting first order dependence with respect to acid.The reaction shows first order dependence with respect to and zero order dependence with respect to , indicating the acid-catalysed enolisation of ketones as the rate-determining step and reaction between enol and NIS as the fast step.The decrease in dielectric constant of the medium slightly enhances the reaction rate.The ρ, ?-relationship in the case of acetophenones is quite linear with ρ = -0.5 indicating the simultaneous operation of equilibrium protonation of ketones and deprotonation of the conjugate acid.The ρ, ?* plot of the different aliphatic ketones is also linear.The order of reactivity of different cyclic ketones studied is cyclohexanone ca. cyclooctanone > cyclopentanone > cycloheptanone.Arrhenius parameters have been computed and the observed isoenthalpic relationship has been discussed.A mechanism consistent with the results has been proposed.
- Radhakrishnamurti, P. S.,Mahapatro, D. K.
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p. 207 - 210
(2007/10/02)
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