- Synthesis, structure, and hydrophosphorylation of π-complexes of hexacarbonyltungsten(0) with cyclohexanone, cyclohexanethione, and N-cyclohexylideneaniline
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New carbonyl π-complexes of tungsten(0) with cyclohexanone, cyclohexanethione, and N-cyclohexylideneaniline were synthesized. Geometric and electronic parameters of the ligands, as well as energy parameters of the complex formation process, were determine
- Kuramshin,Pavlova,Cherkasov
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- CeCl3?7H2O-catalysed hydrophosphonylation of aldehydes and ketones: An expeditious route to α-hydroxyphosphonates under solvent-free conditions
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A cerium(III) chloride-catalysed expeditious synthesis of α-hydroxyphosphonates via a modified Abramov synthetic protocol has been developed. The scope of the current protocol is broad, with a range of aromatic, α,β-unsaturated and heterocyclic aldehydes
- Mahesh,Sharma, Rupali,Kour, Parteek,Kumar, Anil
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p. 1091 - 1097
(2019/07/04)
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- A simple heterogeneous catalyst for phosphite addition on carbonyl groups
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A cheap and easily recoverable heterogeneous catalyst could efficiently trigger C-P bond formation by selective addition of phosphites to the carbonyl group of aldehydes and ketones. The reactions afford the desired products in good to excellent yields an
- Santacroce, Veronica,Paris, Emanuele,Cauzzi, Daniele,Maggi, Raimondo,Maestri, Giovanni
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supporting information
p. 463 - 466
(2016/02/18)
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- Syntheses of bimetallic lanthanide bis(amido) complexes stabilized by bridged bis(guanidinate) ligands and their catalytic activity toward the hydrophosphonylation reaction of aldehydes and ketones
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A series of bimetallic lanthanide bis(amido) complexes stabilized by bridged bis(guanidinate) ligands {[(Me3Si)2N]2Ln[(RN)2-CN(CH2)2]}2 [R= i Pr, Ln=Sm (1), Yb (2), Y
- Nie, Kun,Liu, Chengwei,Zhang, Yong,Yao, Yingming
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p. 1451 - 1460
(2015/09/02)
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- C-H hydroxylation of phosphonates with oxygen in [bmIm]OH to produce quaternary α-hydroxy phosphonates
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A highly efficient and mild [bmIm]OH-catalyzed α-hydroxylation of phosphonates using O2 as the oxygen source is described. The employment of ionic liquid under mild reaction conditions makes this transformation green and practical. Especially, this reaction provided a novel and convenient methodology for the construction of quaternary α-hydroxy phosphonates.
- Li, Xiangguang,Jin, Cheng,Gu, Lijun
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p. 2443 - 2447
(2015/05/04)
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- The catalytic aerobic synthesis of quaternary α-hydroxy phosphonates via direct hydroxylation of phosphonate compounds
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A highly efficient Cu-catalyzed direct hydroxylation of phosphonate compounds has been developed. This transformation provides a powerful method for the synthesis of quaternary α-hydroxy phosphonates in good yields. The direct transformation process, regiospecific selectivity, and good tolerance to a variety of substituents make it an alternative approach to the reported protocols.
- Gu, Lijun,Jin, Cheng,Zhang, Hongtao
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supporting information
p. 1579 - 1582
(2015/03/18)
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- Synthesis of quaternary α-hydroxy phosphonates via direct hydroxylation of phosphonate compounds
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It was found for the first time that Cs2CO3 serves as highly efficient catalyst for the direct hydroxylation reactions of phosphonates under mild conditions. This reaction provides an efficient approach to quaternary α-hydroxy phosph
- Liu, Jiyan,Wang, Wei,Wang, Rui,Gu, Lijun
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supporting information
p. 559 - 562
(2015/05/27)
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- Lanthanide anilido complexes: Synthesis, characterization, and use as highly efficient catalysts for hydrophosphonylation of aldehydes and unactivated ketones
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Lanthanide anilido complexes stabilized by the 2,6-diisopropylanilido ligand have been synthesized and characterized, and their catalytic activity for hydrophosphonylation reaction was explored. A reaction of anhydrous LnCl 3 with 5 equivalents
- Liu, Chengwei,Qian, Qinqin,Nie, Kun,Wang, Yaorong,Shen, Qi,Yuan, Dan,Yao, Yingming
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p. 8355 - 8362
(2014/06/09)
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- N -BuLi as a highly efficient precatalyst for hydrophosphonylation of aldehydes and unactivated ketones
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It was found for the first time that organic alkali metal compounds serve as highly efficient precatalysts for the hydrophosphonylation reactions of aldehydes and unactivated ketones with dialkyl phosphite under mild conditions. For ketone substrates, a reversible reaction was observed, and the influence of catalyst loading and reaction temperature on the reaction equilibrium was studied in detail. Overall, the hydrophosphonylation reactions catalyzed by 0.1 mol % n-BuLi were completed within 5 min for a broad range of substrates and generated a series of α-hydroxy phosphonates in high yields.
- Liu, Chengwei,Zhang, Yu,Qian, Qinqin,Yuan, Dan,Yao, Yingming
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supporting information
p. 6172 - 6175
(2015/01/09)
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- Synthesis and characterization of amidate rare-earth metal amides and their catalytic activities toward hydrophosphonylation of aldehydes and unactivated ketones
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Two novel amidate rare-earth metal amides Ln[N(SiMe3)2](κ2-L1)2(THF) (L1 = C6H5C(O)NC6H3(iPr)2) (Ln = Yb (1), Y (2)) were p
- Zhao, Lu,Ding, Hao,Zhao, Bei,Lu, Chengrong,Yao, Yingming
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- Synthesis and characterization of organolanthanide complexes with a calix[4]-pyrrolyl ligand and their catalytic activities toward hydrophosphonylation of aldehydes and unactivated ketones
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The alkali metal salt free dinuclear trivalent lanthanide amido complexes (η5:η1:η5:η1-Et 8-calix[4]-pyrrolyl){LnN(SiMe3)2}2 (Ln = Nd (2), Sm (3), Gd (4)) were prepare
- Zhou, Shuangliu,Wang, Hengyu,Ping, Jian,Wang, Shaowu,Zhang, Lijun,Zhu, Xiancui,Wei, Yun,Wang, Fenhua,Feng, Zhijun,Gu, Xiaoxia,Yang, Song,Miao, Hui
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experimental part
p. 1696 - 1702
(2012/04/23)
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- New catalyst for phosphonylation of C=X electrophiles
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Pyridinium perchlorate is found to be an efficient and recyclable catalyst for the reaction of trialkyl phosphites with various C=X electrophiles (aldehydes, ketones, ketophosphonates, imines, isocyanates, isothiocyanates, activated alkenes) to afford cor
- Kolodiazhnyi, Oleg I.,Kolodiazhna, Olga O.
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experimental part
p. 1637 - 1649
(2012/05/05)
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- Pyridinium perchlorate: A new catalyst for the reaction of trialkyl phosphites with the C=X electrophiles
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Pyridinium perchlorate is an effective catalyst for the reaction of trialkyl phosphites with various C=X electrophiles: aldehydes, ketones, ketophosphonates, imines, isocyanates, isothiocyanates, and activated alkenes. The reaction leads to the formation
- Kolodyazhnaya,Kolodyazhnyi
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scheme or table
p. 307 - 314
(2011/06/27)
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- An efficient method for the phosphonation of C=X compounds
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Reaction of trialkyl phosphites with C=X electrophiles (aldehydes, ketones, ketophosphonates, aldimines, ketimines, isocyanates, isothiocyanates, and activated olefins) in the presence of amines and anilines hydrohalides was studied. We found that pyridine hydrohalides effectively activate the reaction of tralkyl phosphites with various C=X electrophiles: aldehydes, ketones, ketophosphonates, aldimines, ketimines, isocyanates, isothiocyanates, and activated olefins. Particularly high activity showed pyridine hydroiodide. This reaction is a convenient method of synthesis of hydroxyphosphonates, aminophosphonates, carbamoylphosphonates, carbamoylthiophosphonates, and methylenebisphosphonates. Pleiades Publishing, Ltd., 2010.
- Kolodyazhnaya,Kolodyazhnaya,Kolodyazhnyi
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experimental part
p. 709 - 722
(2011/01/08)
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- Catalytic synthesis of α-hydroxyphosphonates
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Reactions of carbonyl compounds of aliphatic, aromatic, and heteroaromatic series with dialkyl phosphites in the presence of DBN were studied under microwave irradiation.
- Kabachnik,Minaeva,Beletskaya
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experimental part
p. 1119 - 1122
(2009/12/03)
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- Aminopyridines as amino components in the catalytic synthesis of α-aminophosphonates
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6h-Aminophosphonates containing alicyclic, aromatic, and heterocyclic fragments were obtained in high yields by the Kabachnick-Fields reaction of the corresponding carbonyl compounds with 2-, 3- and 4-aminopyridines and diethyl phosphite using tetra- tert
- Matveeva,Podrugina,Kolesnikova,Borisenko,Zefirov
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experimental part
p. 119 - 125
(2010/06/12)
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- The preparation of dialkyl 1-hydroxyalkylphosphonates in the reaction of trialkyl phosphites with oxonium salts derived from aldehydes or ketones
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The reaction of trialkyl phosphites with aldehydes or ketones in the presence of hydrogen chloride gives dialkyl 1-hydroxyalkylphosphonates via Arbusov-like reaction of oxonium salts derived from aldehydes or ketones. This reaction is a very convenient instant method for the preparation of dialkyl 1-hydroxyalkylphosphonates with a good yield as an alternative to the well-known Abramov reaction. Georg Thieme Verlag Stuttgart.
- Goldeman, Waldemar,Soroka, Miroslaw
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p. 3019 - 3024
(2008/02/08)
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- Lithium perchlorate diethyl ether solution: A highly efficient media for the abramov reaction
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The α-hydroxy phosphonates are readily prepared by treating aromatic or aliphatic aldehydes and ketones with trialkylphosphite in the presence of trimethylsilylchloride in a very short time and in almost quantitative yields.
- Azizi, Najmedin,Saidi, Mohammad R.
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p. 1255 - 1259
(2007/10/03)
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- 1,5,7-Triazabicyclo[4.4.0]dec-1-ene (TBD), 7-methyl-TBD (MTBD) and the polymer-supported TBD (P-TBD): Three efficient catalysts for the nitroaldol (Henry) reaction and for the addition of dialkyl phosphites to unsaturated systems
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The 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) and its 7-methyl derivative (MTBD) have been proven to be of great synthetic utility as catalysts in the nitroaldol (Henry) reaction and for the addition of dialkyl phosphites to a variety of carbonyl compounds. The catalysts were in many cases superior to the parent tetramethylguanidine (TMG). In general the reaction proceeds in a few minutes at 0°C. The polymer-supported-TBD (P- TBD) was also proven to be an efficient promoter of the above cited nucleophilic additions. (C) 2000 Elsevier Science Ltd.
- Simoni, Daniele,Rondanin, Riccardo,Morini, Massimo,Baruchello, Riccardo,Invidiata, Francesco Paolo
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p. 1607 - 1610
(2007/10/03)
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- Tetramethylguanidine (TMG)-catalyzed addition of dialkyl phosphites to α,β-unsaturated carbonyl compounds, alkenenitriles, aldehydes, ketones and imines
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Tetramethylguanidine-catalyzed addition of dialkyl phosphites to α,β- unsaturated carbonyl compounds, alkenenitriles, aldehydes and ketones constitutes a practical route to a variety of phosphonate synthons. The very mild conditions employed, together with the short reaction times, make the procedure highly versatile and tolerant to a range of functionalities. The proposed methodology is also convenient for the preparation of α- aminophosphonates.
- Simoni, Daniele,Invidiata, Francesco Paolo,Manferdini, Monica,Lampronti, Ilaria,Rondanin, Riccardo,Roberti, Marinella,Pollini, Gian Piero
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p. 7615 - 7618
(2007/10/03)
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- The synthesis of alpha-hydroxyphosphonates for phosphate support without solvents
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The synthesis of α-hydroxyphosphonates has been carried out with a high yield at room temperature, using natural phosphate, natural phosphate doped with potassium fluoride and sodium phosphate dodecahydrate without solvents.
- Sebti,Rhihil,Saber,Laghrissi,Boulaajaj
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p. 3999 - 4000
(2007/10/03)
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- Nucleophilic addition to carbonyl compounds, competition between hard (amine) and soft (phosphite) nucleophile
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In the Kabachnik Fields reaction mixture, two nucleophiles: dialkyl phosphite and the amine compete for the electrophilic carbonyl compound. Reaction mixture composition studies, kinetic studies as well as theoretical calculations, indicate that the softe
- Gancarz, Roman
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p. 10627 - 10632
(2007/10/02)
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- AN UNEXPECTED REACTIVITY OF SIMPLE HETEROGENEOUS MIXTURE OF γ-ALUMINA AND POTASSIUM FLUORIDE : 1-HYDROXYALKANE PHOSPHONIC ESTERS SYNTHESIS FROM NON-ACTIVATED KETONES IN "DRY MEDIA".
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1-Hydroxyalkane phosphonic esters are readily obtained from non-activated ketones and dialkylphosphites by absorbing them together on a heterogeneous γ-alumina-potassium fluoride mixture.
- Texier-Boullet, Francoise,Lequitte, Maryvonne
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p. 3515 - 3516
(2007/10/02)
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- Mesylate Derivatives of α-Hydroxy Phosphonates. Formation of Carbocations Adjacent to the Diethyl Phosphonate Group
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Mesylates 3-6 have been prepared and reacted in a variety of solvents.Product, rate, and solvent effect studies implicate carbocationic intermediates in these solvolyses despite the electron-withdrawing PO(OEt)2 group.Mesylate 3 gave exclusive substitution products.Optically active 3 gave racemic products on trifluoroacetolysis. α-Deuterium isotope effects were also in line with a cationic intermediate.Mesylate 4 gave some elimination product, 27, along with the substitution product 28, also via a cationic intermediate.Mesylates 5 and 6 gave exclusive elimination products.A β-deuterium isotope effect study gave a kH6/kD6 value of 2.8.This isotope effect, along with a small m value (0.45), suggested the intermediacy of a reversibly formed ion pair which subsequently loses a proton.This mechanism represents the merging of the classical E1 mechanism and the E2C(+) mechanism, the latter representing the cationic counterpart of the E1cb mechanism.Analysis of the solvolysis rates of 3 and 4 led to the conclusion that cationic intermediates are formed quite easily.Reasons are suggested for this unexpectedly facile generation of cations adjacent to the potent electron-withdrawing PO(OEt)2 substituent.
- Creary, Xavier,Geiger, Cristina C.,Hilton, Kathryn
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p. 2851 - 2858
(2007/10/02)
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