- A comparison of reactivity of (EtO)2P(O)CH2I with related non-phosphorus-containing iodides in the radical iodine atom transfer addition
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Based on competitive reactions and 1H NMR measurements, it was found that (EtO)2P(O)CH2I is at least 2-3 orders of magnitude less reactive than other non-phosphorus iodides of the EWG-CH2I type (EWG = NC COOMe,
- Balczewski, Piotr,Bialas, Tomasz,Szadowiak, Aldona
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Read Online
- 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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- 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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p. 1218 - 1220
(2019/07/16)
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- Rapid and efficient one-pot microwave-assisted synthesis of 2-phenylimidazo[1,2-a]pyridines and 2-phenylimidazo[1,2-a]quinoline in water–PEG-400
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An effective, expeditious, environmentally benign one-pot synthesis of 2-phenylimidazo[1,2-a]pyridines and 2-phenylimidazo[1,2-a]quinoline from easily available starting materials as aromatic carbonyl compound, 2-amino pyridine, succinamide, and in situ g
- Jadhav, Santosh A.,Shioorkar, Mahesh G.,Chavan, Omprakash S.,Sarkate, Aniket P.,Shinde, Devanand B.
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supporting information
p. 285 - 290
(2017/02/10)
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- Mild and General Synthesis of Pyrrolo[2,1-a]isoquinolines and Related Polyheterocyclic Frameworks from Pyrrole Precursors Derived from a Mechanochemical Multicomponent Reaction
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The combination of a three-component, solvent-free pyrrole synthesis performed under mechanochemical conditions with a TMSOTf-catalyzed oxonium-mediated cyclization gave general access to pyrrolo[2,1-a]isoquinoline derivatives under very mild conditions.
- Leonardi, Marco,Villacampa, Mercedes,Menéndez, J. Carlos
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p. 2570 - 2578
(2017/03/14)
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- Expeditious one-pot multicomponent microwave-assisted green synthesis of substituted 2-phenyl Quinoxaline and 7-bromo-3-(4-ethylphenyl) pyrido[2,3-b]pyrazine in water–PEG and water–ethanol
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An eco-friendly, expeditious one-pot multicomponent synthesis of substituted 2-phenyl quinoxaline and 7-bromo-3-(4-ethylphenyl) pyrido[2,3-b]pyrazine 4a–k in water–ethanol from easily available starting materials as acetophenone 1, succinamide 2, aromatic
- Jadhav, Santosh A.,Sarkate, Aniket P.,Shioorkar, Mahesh G.,Shinde, Devanand B.
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p. 1661 - 1667
(2017/09/08)
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- First Catalyzed Hydration of Haloalkynes by a Recyclable Catalytic System
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The hydration of haloalkynes to give α-halomethyl ketones was achieved based on a combination of a Cu(OAc)2 catalyst and a TFA (trifluoroacetic acid) promoter. This is the first synthesis of chloro/bromo/iodo methyl ketones through a hydration reaction catalyzed by a recyclable catalytic system. The catalytic system has a wide substrate scope and excellent chemoselectivity, and the procedure can also be scaled up.
- Zou, Huaxu,He, Weibao,Dong, Qizhi,Wang, Ruijia,Yi, Niannian,Jiang, Jun,Pen, Dongming,He, Weimin
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p. 116 - 121
(2016/01/26)
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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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- 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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p. 12186 - 12190
(2015/02/19)
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- Direct one-pot synthesis of zolimidine pharmaceutical drug and imidazo[1,2-a]pyridine derivatives via I2/CuO-promoted tandem strategy
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An efficient one-pot synthetic protocol was developed for the synthesis of imidazo[1,2-a]pyridines from easily available starting materials: Aromatic ketones, α,β-unsaturated ketones, β-keto esters and 2-aminopyridines. The present reaction proceeded well in MeOH under the media of I2/CuO. By using this method, the marketed drug zolimidine could be prepared easily with 95% yield. All these target products were characterized by NMR, HRMS and IR spectra. Furthermore, the target compound 3fa was determined by X-ray crystallographic analysis.
- Cai, Qun,Liu, Mei-Cai,Mao, Bi-Ming,Xie, Xuan,Jia, Feng-Cheng,Zhu, Yan-Ping,Wu, An-Xin
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p. 881 - 884
(2015/03/04)
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- Uranyl Schiff base complexes as new heterogeneous catalysts for halogen exchange reactions between alkyl halides and elemental halogens
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Mild and effective procedure for the halogen exchange reaction of alkyl halides with elemental iodine and bromine catalyzed with uranyl Schiff base complexes in various aprotic solvents was developed. Corresponding alkyl bromides and iodides were obtained with high yields within 20—70 min. The structures of the target products were confirmed by physical and spectroscopic data.
- Naeimi,Nazifi
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p. 1814 - 1818
(2016/05/11)
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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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- 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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- 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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- 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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- A direct method for the synthesis of indolizine derivatives from easily available aromatic ketones, pyridines, and acrylonitrile derivatives
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A concise and efficient strategy has been proposed to synthesize indolizine derivatives from easily available aryl or heteroaryl methyl ketones, pyridines, and acrylonitriles. The mechanistic pathway involved the integration of iodination, pyridinium ylid
- Cai, Qun,Zhu, Yan-Ping,Gao, Yang,Sun, Jing-Jing,Wu, An-Xin
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supporting information
p. 414 - 419
(2013/07/25)
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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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- A multipathway coupled domino strategy: Metal-free oxidative cyclization for one-pot synthesis of 2-acylbenzothiazoles from multiform substrates
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A multipathway coupled domino strategy has been developed for the efficient synthesis of 2-acylbenzothiazoles from multiform substrates arylethenes, arylacetylenes, 2-hydroxy-aromatic ketones, and carbinols via four distinct pathways. Through a logical coupled oxidation/heterocyclization domino process, a variety of 2-acylbenzothiazoles were synthesized free of metal in one pot.
- Zhu, Yan-Ping,Jia, Feng-Cheng,Liu, Mei-Cai,Wu, An-Xin
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p. 4414 - 4417
(2012/10/29)
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- Solid-phase organic synthesis of α-iodo ketones using recyclable resin-bound selenium bromide
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A novel facile method for the traceless solid-phase synthesis of α-iodo ketones using a recyclable resin-bound selenium bromide reagent is reported. Various ketones and α-dicarbonyl compounds can be converted to the corresponding α-iodo-substituted compou
- Mao, Xue-Chun,Liu, Xiao-Ling,Deng, Qiang,Sheng, Shou-Ri
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experimental part
p. 100 - 102
(2012/04/23)
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- IBX/Imediated reaction of sodium arenesulfinates with alkenes: Facile synthesis of β-keto sulfones
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A direct synthesis of -keto sulfones from alkenes is described. A combination of o-iodoxybenzoic acid/iodine (IBX/I was found to mediate the reactions of alkenes with arenesulfinates to yield -keto sulfones in good yields via a one-pot reaction. Georg Thieme Verlag Stuttgart · New York.
- Samakkanad, Natthapol,Katrun, Praewpan,Techajaroonjit, Thanachart,Hlekhlai, Sornsiri,Pohmakotr, Manat,Reutrakul, Vichai,Jaipetch, Thaworn,Soorukram, Darunee,Kuhakarn, Chutima
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experimental part
p. 1693 - 1699
(2012/07/03)
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- Coupling of methyl ketones and primary or secondary amines leading to α-ketoamides
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A metal-free oxidative coupling of methyl ketones and primary or secondary amines to α-ketoamides has been developed. Four intermediates, α-iodoketone, α-aminoketone, iminium intermediate, and α-hydroxy amine have been identified through a series of control experiments. The atom-economic methodology can be scaled-up, tolerates a variety of functional groups, and is operationally simple.
- Wei, Wei,Shao, Ying,Hu, Huayou,Zhang, Feng,Zhang, Chao,Xu, Yuan,Wan, Xiaobing
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p. 7157 - 7165
(2012/11/07)
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- I2/CuO-catalyzed tandem cyclization strategy for one-pot synthesis of substituted 2-aminothiozole from easily available aromatic ketones/α,β-unsaturated ketones and thiourea
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A concise and efficient one-pot process from easily available methyl ketones/unsaturated methyl ketones and thiourea was developed for the synthesis of 2-aminothiazoles under the media of I2/CuO. The method can highly stereoselectivity obtain the E-isomers of 4-ethenyl-2-aminothiazoles (5a-f). All these target molecules were characterized by NMR, HRMS and IR spectra. Furthermore, the target compounds 3c and 5b were further determined by X-ray crystallographic analysis.
- Zhu, Yan-Ping,Yuan, Jing-Jing,Zhao, Qin,Lian, Mi,Gao, Qing-He,Liu, Mei-Cai,Yang, Yan,Wu, An-Xin
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supporting information; experimental part
p. 173 - 178
(2012/01/05)
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- Logic design and synthesis of quinoxalines via the integration of iodination/oxidation/cyclization sequences from ketones and 1,2-diamines
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A novel protocol for the synthesis of quinoxalines has been developed from simple ketones and 1,2-diamines. This process underwent a logic approach to bis-substituted quinoxalines via a consecutive iodination/Kornblum oxidation/cyclization in the presence of I2/CuO/DMSO and to mono-substituted quinoxalines via an iodination/cyclization/aromatization in the presence of I2/CuO/K3PO4·3H 2O.
- Lian, Mi,Li, Qi,Zhu, Yanping,Yin, Guodong,Wu, Anxin
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p. 9598 - 9605
(2012/11/07)
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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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- Functionalized 3(2H)-furanones via photooxygenation of (β-keto)-2- substituted furans: Application to the biomimetic synthesis of merrekentrone C
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Photooxygenation of (β-keto)-2-substituted furans leads, in a one pot operation, to functionalized 3(2H)-furanones with good to excellent yields. This methodology was applied as a key-step to the concise and biomimetic synthesis of the sesquiterpene merre
- Gryparis, Charis,Lykakis, Ioannis N.,Efe, Christina,Zaravinos, Ioannis-Panayotis,Vidali, Theonymphi,Kladou, Eugenia,Stratakis, Manolis
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supporting information; experimental part
p. 5655 - 5658
(2011/09/16)
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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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experimental part
p. 300 - 302
(2012/01/14)
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- Switching reversibility to irreversibility in glycogen synthase kinase 3 inhibitors: Clues for specific design of new compounds
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Development of kinase-targeted therapies for central nervous system (CNS) diseases is a great challenge. Glycogen synthase kinase 3 (GSK-3) offers a great potential for severe CNS unmet diseases, being one of the inhibitors on clinical trials for different tauopathies. Following our hypothesis based on the enhanced reactivity of residue Cys199 in the binding site of GSK-3, we examine here the suitability of phenylhalomethylketones as irreversible inhibitors. Our data confirm that the halomethylketone unit is essential for the inhibitory activity. Moreover, addition of the halomethylketone moiety to reversible inhibitors turned them into irreversible inhibitors with IC50 values in the nanomolar range. Overall, the results point out that these compounds might be useful pharmacological tools to explore physiological and pathological processes related to signaling pathways regulated by GSK-3 opening new avenues for the discovery of novel GSK-3 inhibitors.
- Perez, Daniel I.,Palomo, Valle,Pérez, Concepción,Gil, Carmen,Dans, Pablo D.,Luque, F. Javier,Conde, Santiago,Martínez, Ana
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experimental part
p. 4042 - 4056
(2011/08/05)
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- Formation of unsymmetrical 1,4-enediones via A focusing domino strategy: Cross-coupling of 1,3-dicarbonyl compounds and methyl ketones or terminal aryl alkenes
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A highly efficient synthesis of unsymmetrical 1,4-enediones from 1,3-dicarbonyl compounds and methyl ketones or terminal aryl alkenes has been developed via a focusing domino strategy. Simple and readily available starting materials, mild reaction conditions, and a very simple operation are advantages of the reaction, which allow straightforward synthesis of a variety of unsymmetrical 1,4-enediones.
- Gao, Meng,Yang, Yan,Wu, Yan-Dong,Deng, Cong,Cao, Li-Ping,Meng, Xiang-Gao,Wu, An-Xin
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supporting information; experimental part
p. 1856 - 1859
(2010/10/03)
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- M-iodosylbenzoic acid as a convenient recyclable hypervalent iodine oxidant for the synthesis of α-iodo ketones by oxidative iodination of ketones
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A convenient procedure for the preparation of -iodo ketones by oxidative iodination of ketones using iodine and m-iodosylbenzoic acid as a recyclable hypervalent iodine oxidant is reported. Various ketones and -dicarbonyl compounds can be iodinated by thi
- Yusubov, Mehman S.,Yusubova, Rosa Y.,Funk, Tatyana V.,Chi, Ki-Whan,Kirschning, Andreas,Zhdankin, Viktor V.
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experimental part
p. 3681 - 3685
(2010/12/20)
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- IBX/I2-mediated oxidation of alkenes and alkynes in water: a facile synthesis of α-iodoketones
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The conversion of alkenes into α-iodoketones has been achieved in good yields and with high regioselectivity by means of iodohydrin formation and subsequent oxidation with 2-iodoxybenzoic acid (IBX) under mild conditions. Aromatic alkynes are also convert
- Yadav, Jhillu S.,Subba Reddy, Basi V.,Singh, Ashutosh P.,Basak, Ashok K.
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scheme or table
p. 5880 - 5882
(2009/04/04)
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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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- Metal catalyst-free direct α-iodination of ketones with molecular iodine
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Ketones are directly converted to the corresponding α-iodoketones in good yields with molecular iodine under metal catalyst-free conditions. A significant difference in the reactivities was observed for aliphatic and aromatic ketones; whereas aliphatic ke
- Rao, Maddali L.N.,Jadhav, Deepak N.
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p. 6883 - 6886
(2007/10/03)
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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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- 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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p. 179 - 180
(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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