- Palladium-catalyzed one-pot phosphorylation of phenols mediated by sulfuryl fluoride
-
We report a general palladium-catalyzed one-pot procedure for the synthesis of phosphonates, phosphinates and phosphine oxides from phenols mediated by sulfuryl fluoride. It features mild conditions, broad substrate scope, high functionality tolerance and water insensitivity. The utility of this procedure has been well demonstrated by gram-scale synthesis, sequential synthesis of click chemistry building blocks, late-stage decoration of drugs and natural products and on-DNA synthesis of phosphine oxide for a DNA-encoded library (DEL).
- Zhang, Yiyuan,Chen, Wanting,Tan, Tingting,Gu, Yuang,Zhang, Shuning,Li, Jie,Wang, Yan,Hou, Wei,Yang, Guang,Ma, Peixiang,Xu, Hongtao
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p. 4588 - 4591
(2021/05/17)
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- Fe-MIL-101 modified by isatin-Schiff-base-Co: a heterogeneous catalyst for C-C, C-O, C-N, and C-P cross coupling reactions
-
A metal-organic framework functionalized with a cobalt-complex is preparedviapost-synthetic modification of Fe-MIL-101-NH2. Initially, Fe-MIL-101-NH2reacted with isatin to produce Fe-MIL-101-isatin-Schiff-base, which can anchor the cobalt by the addition of cobalt acetate. The resulting MOF-Co catalyst is characterized by employing multiple techniques. This new modified MOF acts as a heterogeneous and recyclable catalyst for efficient Ullmann, Buchwald-Hartwig, Hirao, Hiyama and Mizoroki-Heck cross-coupling reactions of several aryl halides/phenylboronic acid/phenyltosylate with phenols, anilines/heterocyclic amines, triethyl phosphite, triethoxyphenylsilane and alkenes and generates the expected coupling products in good to high yields.
- Farrokhi, Alireza,Rouzifar, Majid,Sansano, José Miguel,Sobhani, Sara
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p. 19963 - 19976
(2021/11/12)
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- Investigation of Immobilization Effects on Ni(P2N2)2Electrocatalysts
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A new synthetic route to complexes of the type Ni(P2N2)22+ with highly functionalized phosphine substituents and the investigation of immobilization effects on these catalysts is reported. Ni(P2N2)22+ complexes have been extensively studied as homogeneous and surface-attached molecular electrocatalysts for the hydrogen evolution reaction (HER). A synthesis based on postsynthetic modification of PArBr2NPh2 was developed and is described here. Phosphonate-modified ligands and their corresponding nickel complexes were isolated and characterized. Subsequent deprotection of the phosphonic ester derivatives provided the first Ni(P2N2)22+ catalyst that can be covalently attached via pendent phosphonate groups to an electrode without involvement of the important pendent amine groups. Mesoporous TiO2 electrodes were surface modified by attachment of the new phosphonate functionalized Ni(P2N2)22+ complexes, and these provided electrocatalytic materials that proved to be competent and stable for sustained HER in aqueous solution at mild pH and low overpotential. We directly compared the new ligand to a previously reported complex that utilized the amine moiety for surface attachment. Using HER as the benchmark reaction, the P-attached catalyst showed a marginally (9-14%) higher turnover number than its N-attached counterpart.
- Brunner, Felix M.,Neville, Michael L.,Kubiak, Clifford P.
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p. 16872 - 16881
(2020/11/27)
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- A hydrophilic heterogeneous cobalt catalyst for fluoride-free Hiyama, Suzuki, Heck and Hirao cross-coupling reactions in water
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A hydrophilic heterogeneous cobalt catalyst of chitosan, denoted as mTEG-CS-Co-Schiff-base, has been successfully prepared. This newly synthesized catalyst was characterized by different methods such as XRD, FE-SEM, TEM, TGA, FT-IR, 13C{1H} CP/MAS NMR, XPS and ICP analyses. The catalyst displayed excellent activity for the palladium and fluoride-free Hiyama, Suzuki, Heck and Hirao reactions of various aryl iodides, bromides and chlorides (i.e., the most challenging aryl halides which are cheaper and more widely available than aryl iodides and bromides) in water. The presence of triethylene glycol tags with hydrophilic character on the Co-complex supported on chitosan provides dispersion of the catalyst particles in water, which leads to higher catalytic performance and also facile catalyst recovery by successive extraction. It was reused for at least six successive runs without any discernible decrease in its catalytic activity or any remarkable changes in catalyst structure. The use of water as a green solvent, without requiring any additive or organic solvent, as well as use of a low cost and abundant cobalt catalyst instead of expensive Pd catalysts along with the catalyst recovery and scalability, make this method favorable from environmental and economic points of view for the C-C and C(sp2)-P coupling reactions. Notably, this is the first report on the application of a cobalt catalyst in Hiyama reactions.
- Sobhani, Sara,Hosseini Moghadam, Hadis,Skibsted, J?rgen,Sansano, José Miguel
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p. 1353 - 1365
(2020/03/11)
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- NAPHTHYRIDINE DERIVATIVES AS PRC2 INHIBITORS
-
Disclosed are compounds of formula (I) or (II) that inhibit Polycomb Repressive Complex 2 (PRC2) activity. In particular, the present invention relates to compounds, pharmaceutical compositions and methods of use, such as methods of treating cancer using the compounds and pharmaceutical compositions of the present invention.
- -
-
Paragraph 0404-0405
(2020/11/03)
-
- IMIDAZO[1,2-C]PYRIMIDINE DERIVATIVES AS PRC2 INHIBITORS FOR TREATING CANCER
-
Disclosed are compounds that inhibit Polycomb Repressive Complex 2 (PRC2) activity. In particular, disclosed are compounds of Formula (I) and pharmaceutical compositions thereof, and methods of using the compounds and pharmaceutical compositions in, for example, methods of treating cancer.
- -
-
Paragraph 0345-0346
(2020/12/29)
-
- PRC2 INHIBITORS
-
The present invention relates to compounds that inhibit Polycomb Repressive Complex 2 (PRC2) activity. In particular, the present invention relates to compounds, pharmaceutical compositions and methods of use, such as methods of treating cancer using the compounds and pharmaceutical compositions of the present invention. (Formula (I))
- -
-
Paragraph 0354-0355
(2019/08/26)
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- Catalyst-free phosphorylation of aryl halides with trialkyl phosphites through electrochemical reduction
-
A catalyst-free electrochemical cross-coupling reaction of aryl halides with trialkyl phosphite has been developed. This reaction proceeds in an undivided cell with a low-cost Ni anode and a graphite cathode under mild and neutral conditions. A wide range of functional groups are well-tolerated and the phosphorylated product can be obtained on the gram scale, showing that this transformation has the potential to be a valuable method for the construction of aromatic carbon-phosphorus bonds.
- Wang, Shuai,Yang, Cheng,Sun, Shuo,Wang, Jianbo
-
supporting information
p. 14035 - 14038
(2019/11/25)
-
- Visible-Light-Mediated Metal-Free Synthesis of Aryl Phosphonates: Synthetic and Mechanistic Investigations
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This work describes a straightforward access to a large variety of aryl phosphonates by the simple combination of diaryliodonium salts with phosphites in the presence of a base and under visible-light illumination. The reaction proceeds smoothly, tolerates various functionalities, and was applied for the synthesis of pharmaceutically relevant compounds. Mechanistic investigations, including EPR, NMR, and DFT calculations, support the postulated reaction mechanism.
- Lecroq, William,Bazille, Pierre,Morlet-Savary, Fabrice,Breugst, Martin,Lalevée, Jacques,Gaumont, Annie-Claude,Lakhdar, Sami
-
supporting information
p. 4164 - 4167
(2018/07/29)
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- Avisible-light-promoted metal-free strategy towards arylphosphonates: Organic-dye-catalyzed phosphorylation of arylhydrazines with trialkylphosphites
-
A visible-light-induced metal-free catalytic system was developed for the synthesis of arylphosphonates starting from arylhydrazines and trialkylphosphites. By using the inexpensive eosin B as catalyst, sub-stoichiometric amounts of DABCO, and ambient air as oxidant, diverse arylphosphonates were obtained under visible-light irradiation. Notably, this catalytic system is suitable for gram-scale reaction by utilizing sunlight as an illumination source.
- Li, Rui,Chen, Xiaolan,Wei, Shengkai,Sun, Kai,Fan, Lulu,Liu, Yan,Qu, Lingbo,Zhao, Yufen,Yu, Bing
-
supporting information
p. 4807 - 4813
(2018/12/11)
-
- Synthesis, characterization and properties of titanium phosphonate clusters
-
Titanium phosphonate clusters were synthesized by the reactions of titanium tetraisopropoxide (Ti(OiPr)4) with arylphosphonic acids (ArPO3H2, Ar = Ph, 1-Nap, 4-MeOPh, 4-FPh, 4-ClPh, 4-BrPh, and 4-BrBn) and H2O in tetrahydrofuran (THF) at room temperature. [Ti4(μ3-O)(OiPr)5(μ-OiPr)3(O3PAr)3]·solv (Ar = Ph (1), 1-Nap (2), 4-MeOPh (3), 4-FPh (4), 4-ClPh (5); solv = thf for 1 and 2 or 2-propanol for 3–5) were isolated as new Ti4P3-type clusters, while Ti7(μ3-O)2(OiPr)6(μ-OiPr)6(O3PBnBr)6 (6) was isolated as a Ti7P6-type cluster. A co-crystal of Ti4P3- (7a) and Ti7P6-type (7b) clusters were obtained when 4-BrPhPO3H2 was used, and [Ti(OiPr)(acac)(O3PPh)]4 (8), a new cage cluster, was obtained when Ti(acac)2(OiPr)2 (Hacac = acetylacetone) was reacted with PhPO3H2.
- Hayami, Ryohei,Sagawa, Takuya,Tsukada, Satoru,Yamamoto, Kazuki,Gunji, Takahiro
-
supporting information
p. 1 - 8
(2018/04/02)
-
- P-arylation of aryl halides by an environmentally compatible method
-
In this paper, palladium-DABCO complex supported on magnetic nanoparticles was successfully used as a new magnetically recoverable heterogeneous catalyst for the synthesis of arylphosphonates via P-arylation of different types of aryl halides (aryl iodides/bromides/chlorides and benzene boronic acid/sulfonate), with phosphite esters (triethyl/triphenyl/tri-iso-propyl/diethyl/diphenyl/di-iso-propyl phosphite) in neat water without using any additive. The heterogeneous catalyst was easily isolated from the reaction mixture by an external magnet and reused five times without significant degradation in its activity.
- Sobhani, Sara,Vahidi, Zahra
-
p. 1280 - 1284
(2017/11/27)
-
- PYRAZOLE DERIVATIVES, COMPOSITIONS AND THERAPEUTIC USE THEREOF
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Compounds of Formula (I): and salts thereof, and methods of use as Janus kinase inhibitors are described herein.
- -
-
Page/Page column 277; 278
(2017/12/13)
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- Nucleophile promoted gold redox catalysis with diazonium salts: C-Br, C-S and C-P bond formation through catalytic Sandmeyer coupling
-
Gold-catalyzed C-heteroatom (C-X) coupling reactions are evaluated without using sacrificial oxidants. Vital to the success of this methodology is the nucleophile-assisted activation of aryldiazonium salts, which could be an effective oxidant for converting Au(i) to Au(iii) even without the addition of an assisting ligand or photocatalyst. By accelerating the reaction kinetics to outcompete C-C homo-coupling or diazonium dediazoniation, gold-catalyzed Sandmeyer reactions were achieved with different nucleophiles, forming C-Br, C-S and C-P bonds in high yields and selectivities.
- Peng, Haihui,Cai, Rong,Xu, Chang,Chen, Hao,Shi, Xiaodong
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p. 6190 - 6196
(2016/09/03)
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- Synthesis of arylphosphonates catalyzed by Pd-imino-Py-γ-Fe2O3 as a new magnetically recyclable heterogeneous catalyst in pure water without requiring any additive
-
A palladium-Schiff base complex immobilized covalently on γ-Fe2O3 (Pd-imino-Py-γ-Fe2O3) was synthesized and characterized by different methods such as XRD (X-ray diffraction), SEM (scanning electron microscopy), TEM (transmission electron microscopy), FT-IR (Fourier transform infrared spectroscopy), TGA (thermogravimetric analysis), ICP (inductively coupled plasma), XPS (X-ray photoelectron spectroscopy), VSM (vibrating sample magnetometer) and elemental analysis. It was used as a new magnetically recyclable heterogeneous Pd catalyst for the synthesis of arylphosphinates via Csp2-P coupling reactions. A wide range of electrophilic benzenes were coupled successfully with triethylphosphite to generate the corresponding products in good to high yields in pure water without using any additive. The true heterogeneous Pd-imino-Py-γ-Fe2O3 could be reused simply with the aid of a magnetic bar for eight consecutive cycles without any drastic loss of its reactivity.
- Sobhani, Sara,Ramezani, Zohreh
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p. 29237 - 29244
(2018/06/06)
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- A new magnetically recoverable heterogeneous palladium catalyst for phosphonation reactions in aqueous micellar solution
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A new heterogeneous palladium complex of 2-aminothiophenol supported on nanomagnetic γ-Fe2O3 was synthesized and characterized using various methods. The catalyst was used as a magnetically recoverable heterogeneous palladium catalyst for phosphonation reactions via C-P bond formation. Using this method, a wide range of electrophilic benzenes was coupled successfully with phosphite esters (triethyl/tri-isopropyl/triphenylphosphite and diethyl/di-isopropyl/diphenylphosphite) in aqueous micellar solution to generate the corresponding arylphosphonates in good to high yields. The catalyst was separated using an external magnet and reused for six consecutive cycles without any significant loss of its reactivity.
- Sobhani, Sara,Zeraatkar, Zohre
-
-
- Modular synthesis of simple cycloruthenated complexes with state-of-the-art performance in p-type DSCs
-
A modular approach based on Suzuki-Miyaura cross coupling and Miyaura borylation has been used to prepare two cyclometallated [Ru(N N)2(C N)]+ complexes which possess either a carboxylic or phosphonic acid group attached via a phenylene spacer to the 4-position of the pyridine ring in the C N ligand. The key intermediate in the synthetic pathway is [Ru(bpy)2(1)]+ where bpy = 2,2′-bipyridine and H1 is 4-chloro-2-phenylpyridine. The crystal structure of [Ru(bpy)2(1)][PF6] is presented. Reaction of [Ru(bpy)2(1)][PF6] with 4-carboxyphenylboronic acid leads to [Ru(bpy)2(H6)][PF6], while the phosphonic acid analogue is isolated as the zwitterion [Ru(bpy)2(H5)]. The cyclometallated complexes have been characterized by mass spectrometry, multinuclear NMR spectroscopy, absorption spectroscopy and electrochemistry. [Ru(bpy)2(5)] adsorbs onto NiO FTO/NiO electrodes (confirmed by solid-state absorption spectroscopy) and its performance in p-type dye-sensitized solar cells (DSCs) has been compared to that of the standard dye P1; two-screen printed layers of NiO give better DSC performances than one layer. Duplicate DSCs containing [Ru(bpy)2(H5)] achieve short-circuit current densities (JSC) of 3.38 and 3.34 mA cm-2 and photoconversion efficiencies (η) of 0.116 and 0.109%, respectively, compared to values of JSC = 1.84 and 1.96 mA cm-2 and η = 0.057 and 0.051% for P1. Despite its simple dye structure, the performance of [Ru(bpy)2(H5)] parallels the best-performing cyclometallated ruthenium(ii) dye in p-type DSCs reported previously (He et al., J. Phys. Chem. C, 2014, 118, 16518) and confirms the effectiveness of a phosphonic acid anchor in the dye and the attachment of the anchoring unit to the pyridine (rather than phenyl) ring of the cyclometallating ligand.
- Brunner, Felix,Marinakis, Nathalie,Wobill, Cedric,Willgert, Markus,Ertl, Cathrin D.,Kosmalski, Tatjana,Neuburger, Markus,Bozic-Weber, Biljana,Glatzel, Thilo,Constable, Edwin C.,Housecroft, Catherine E.
-
p. 9823 - 9833
(2016/11/02)
-
- Phosphonamide pyrabactin analogues as abscisic acid agonists
-
A four step synthesis towards novel phosphonic pyrabactin analogues is presented. Via a stomatal closure and germination assay, the ability of the analogues to selectively induce the ABA-signaling pathway was demonstrated.
- Van Overtveldt,Heugebaert,Verstraeten,Geelen,Stevens
-
supporting information
p. 5260 - 5264
(2015/05/13)
-
- A Pd complex of a NNN pincer ligand supported on γ-Fe2O3@SiO2 as the first magnetically recoverable heterogeneous catalyst for C-P bond forming reactions
-
A Pd complex of a NNN pincer ligand supported on γ-Fe2O3@SiO2 as a new phosphine-free Pd catalyst was synthesized and characterized by different methods such as SEM, TEM, FT-IR, TGA, ICP, XRD, XPS and elemental analysis. The synthesized catalyst was successfully used as the first magnetically recoverable heterogeneous catalyst for the synthesis of arylphosphonates via C-P bond formation by a cross-coupling reaction of different electrophilic benzenes with phosphite esters under solvent-free conditions.
- Sobhani, Sara,Vahidi, Zahra,Zeraatkar, Zohre,Khodadadi, Samaneh
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p. 36552 - 36559
(2015/05/05)
-
- Pd-catalyzed P-arylation of triarylantimony dicarboxylates with dialkyl H-phosphites without a base: Synthesis of arylphosphonates
-
The reaction of triarylantimony diacetates [Ar3Sb(OAc)2] with dialkyl H-phosphites [H-PO(OR)2] in the presence of a Pd(PPh3)4 (5 mol%) catalyst led to the formation of arylphosphonates in moderate to excellent yield under base-free conditions. This reaction is the first example of carbon-phosphorus bond formation by using an organoantimony compound as a pseudo-halide.
- Matsumura, Mio,Dong, Yuqiang,Kakusawa, Naoki,Yasuike, Shuji
-
p. 130 - 133
(2015/02/19)
-
- PYRABACTIN ANALOGUES TO MODULATE PLANT DEVELOPMENT
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The present invention relates to compounds which can be used to control plant development. Indeed, the present invention discloses a new class of pyrabactin analogues which have a physiological effect on -for example- seed germination, and/or stomatal closure, and/or have developmental effects on root and shoot development and organogenesis. Hence, the latter compounds can be used to control plant development such as -for example- increasing the tolerance of plants to drought stress or to control physiological phenomena such as pre-harvest sprouting, tolerance to pathogens etc.
- -
-
Page/Page column 11; 12; 13
(2015/09/23)
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- Palladium-catalyzed desulfitative cross-coupling reaction of sodium arylsulfinates with H-phosphonate diesters
-
A novel and convenient palladium-catalyzed cross-coupling reaction of H-phosphonate diesters with sodium arylsulfinates was developed via desulfitation in the presence of silver carbonate and tetra-butylammonium chloride. This method is highly efficient and provides a rapid access to a broad spectrum of arylphosphonate diesters in good to excellent yields.
- Miao, Tao,Wang, Lei
-
supporting information
p. 967 - 971
(2014/04/03)
-
- Palladium-catalyzed desulfitative C-P coupling of arylsulfinate metal salts and H-phosphonates
-
Catalyzed by palladium(ii) chloride, a diverse range of arylsulfinate sodium, potassium, lithium, silver, zinc, and copper salts undergo desulfination/C-P coupling with H-phosphonates, in the presence of silver(i) carbonate as oxidant, to produce useful arylphosphonates under microwave irradiation. the Partner Organisations 2014.
- Li, Junchen,Bi, Xiaojing,Wang, Hongmei,Xiao, Junhua
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p. 19214 - 19217
(2014/05/20)
-
- Towards the next generation of dual Bcl-2/Bcl-xL inhibitors
-
Structural modifications of the left-hand side of compound 1 were identified which retained or improved potent binding to Bcl-2 and Bcl-x L in in vitro biochemical assays and had strong activity in an RS4;11 apoptotic cellular assay. For example, sulfoxide diastereomer 13 maintained good binding affinity and comparable cellular potency to 1 while improving aqueous solubility. The corresponding diastereomer (14) was significantly less potent in the cell, and docking studies suggest that this is due to a stereochemical preference for the RS versus SS sulfoxide. Appending a dimethylaminoethoxy side chain (27) adjacent to the benzylic position of the biphenyl moiety of 1 improved cellular activity by approximately three-fold, and this activity was corroborated in cell lines overexpressing Bcl-2 and Bcl-xL.
- Varnes, Jeffrey G.,Gero, Thomas,Huang, Shan,Diebold, R. Bruce,Ogoe, Claude,Grover, Paul T.,Su, Mei,Mukherjee, Prasenjit,Saeh, Jamal Carlos,Macintyre, Terry,Repik, Galina,Dillman, Keith,Byth, Kate,Russell, Daniel John,Ioannidis, Stephanos
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p. 3026 - 3033
(2014/06/24)
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- First reusable ligand-free palladium catalyzed C-P bond formation of aryl halides with trialkylphosphites in neat water
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A reusable ligand-free palladium catalyzed phosphonation of aryl iodides, bromides and chlorides with trialkylphosphites is described for the first time in neat water. The aryl phosphonates are obtained in good to excellent yields. The reaction can be also performed with Ni(II) with longer reaction time. The role of tetrabutylammonium bromide in this reaction as reducing agent for generation of Pd(0) at room temperature is also demonstrated. Pd(0)/TBAB was easily reused for three runs without decreasing the efficiency.
- Iranpoor, Nasser,Firouzabadi, Habib,Rajabi Moghadam, Khashayar,Motavalli, Somayeh
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p. 55732 - 55737
(2015/02/05)
-
- A copper-catalyzed variant of the Michaelis-Arbuzov reaction
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As part of our studies on copper-catalyzed arylation of nucleophiles, we report on Michaelis-Arbuzov reactions with a novel catalytic system, featuring a copper(I) salt as precatalyst without any additional ligand. This procedure is an interesting alternative to the use of expensive and toxic transition metals (nickel, palladium) traditionally used as catalysts in Michaelis-Arbuzov reactions. Our approach allows the synthesis from triethylphosphite, diethyl aryl phosphonite, and diaryl ethylphosphinite of various aryl phosphonates, aryl phosphinates, and aryl phosphine oxides, respectively. These families of compounds are essential owing to their respective importance in bioorganic and medical chemistry, their applicability as flame retardants, and their usability in coordination chemistry and catalysis. Copper load of this! The first copper-catalyzed Michaelis-Arbuzov reactions are described. The methodology is ligand-free and allows the direct synthesis of various aryl phosphonates, aryl phosphinates, and aryl phosphine oxides from aryl iodides.
- Ballester, Jorge,Gatignol, Jeremie,Schmidt, Guntram,Alayrac, Carole,Gaumont, Annie-Claude,Taillefer, Marc
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p. 1549 - 1552
(2014/06/24)
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- Copper-catalyzed P-arylation via direct coupling of diaryliodonium salts with phosphorus nucleophiles at room temperature
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A new method for copper-catalyzed P-C bond formation through reaction of phosphorus nucleophiles with diaryliodonium salts at room temperature is described. Most target products are obtained with this method in high yields within a short reaction time of 10 min. It can be easily adapted to large-scale preparations. When unsymmetrical iodonium salts are employed, nucleophilic substitution occurs preferentially on the sterically hindered aromatic ring or the more electron-deficient ring.
- Xu, Jian,Zhang, Pengbo,Gao, Yuzhen,Chen, Yiyin,Tang, Guo,Zhao, Yufen
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p. 8176 - 8183
(2013/09/12)
-
- Arenediazonium tetrafluoroborates in palladium-catalyzed C-P bond-forming reactions. Synthesis of arylphosphonates, -phosphine oxides, and -phosphines
-
A novel palladium-catalyzed synthesis of arylphosphonates from arenediazonium tetrafluoroborates and triethylphosphite or diethylphosphite is presented. The reaction tolerates useful substituents including bromo, chloro, nitro, ether, cyano, keto, and ester groups, can be performed as a one-pot process from anilines omitting the isolation of arenediazonium salts, and can be extended to the preparation of arylphosphine oxides and arylphosphines.
- Berrino, Roberta,Cacchi, Sandro,Fabrizi, Giancarlo,Goggiamani, Antonella,Stabile, Paolo
-
supporting information; experimental part
p. 4518 - 4520
(2010/11/17)
-
- Microwave-promoted palladium(II)-catalyzed C-P bond formation by using arylboronic acids or aryltrifluoroborates
-
The first PdII-catalyzed P arylation has been performed by using palladium acetate, the rigid bidentate ligand dmphen (dmphen=2,9-dimethyl-1,10- phenanthroline), and without the addition of base or acid. Couplings of arylboronic acids or aryl t
- Andaloussi, Mounir,Lindh, Jonas,Saevmarker, Jonas,Sjoeberg, Per J. R.,Larhed, Mats
-
supporting information; experimental part
p. 13069 - 13074
(2010/05/19)
-
- Preparation of arylphosphonates by palladium(O)-catalyzed cross-coupling in the presence of acetate additives: Synthetic and mechanistic studies
-
An efficient protocol for the synthesis of arylphosphonate diesters via a palladium-catalyzed cross-coupling of H-phosphonate diesters with aryl electrophiles, promoted by acetate ions, was developed. A significant shortening of the cross-coupling time in the presence of the added acetate ions was achieved for bidentate and monodentate supporting ligands, and for different aryl electrophiles (iodo, bromo and triflate derivatives). The reaction conditions were optimized in terms of amount of the catalyst, supporting ligands, and source of the acetate ion used. Various arylphosphonates, including those of potential biological significance, were synthesized using this newly developed protocol. Some mechanistic aspects of the investigated reactions are also discussed.
- Kalek, Marcin,Jezowska, Martina,Stawinski, Jacek
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experimental part
p. 3207 - 3216
(2010/04/26)
-
- ORGANOMETAL BENZENEPHOSPHONATE COUPLING AGENTS
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The invention relates to chemical genera of organometal benzenephosphonates useful in cross-coupling organic synthesis, having general formula (I): where R is selected from boron, zinc, tin and silicon residues.
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-
Page/Page column 22-23
(2008/06/13)
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- CaSR ANTAGONIST
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The present invention provides a compound having a calcium-sensitive receptor antagonistic action, a pharmaceutical composition containing the compound, particularly a calcium receptor antagonist and a therapeutic drug for osteoporosis. A compound represented by the following formula (1), a pharmaceutically acceptable salt thereof or an optically active form thereof: wherein each symbol is as defined in the description.
- -
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Page/Page column 60
(2008/06/13)
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- A versatile and efficient ligand for copper-catalyzed formation of C-N, C-O, and P-C bonds: Pyrrolidine-2-phosphonic acid phenyl monoester
-
A new and readily available bidentate ligand, namely, pyrrolidine-2- phosphonic acid phenyl monoester (PPAPM), has been developed for the copper-catalyzed formation of C-N, C-O, and P-C bonds, and various N-, O-, and P-arylation products were synthesized in good to excellent yields by using the CuI/PPAPM catalyst system. Addition of the PPAPM ligand greatly increases the reactivity of the copper catalyst, and the resulting versatile and efficient catalyst system is of widespread and practical application in cross-coupling reactions.
- Rao, Honghua,Jin, Ying,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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p. 3636 - 3646
(2008/02/03)
-
- Proline/pipecolinic acid-promoted copper-catalyzed P-arylation
-
We have developed a convenient and efficient approach for P-arylation of organophosphorus compounds containing P-H. Using commercially available and inexpensive proline and pipecolinic acid as the ligands greatly improved the efficiency of the coupling reactions, so the method can provide an entry to arylphosphonates, arylphosphinates and arylphosphine oxides.
- Huang, Cheng,Tang, Xu,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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p. 5020 - 5022
(2007/10/03)
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- Synthesis of bridged oligothiophenes: Toward a new class of thiophene-based electroactive surfactants
-
(Matrix presented) A series of bridged oligothiophenes have been synthesized. Their novel molecular architecture, comprising two oligothiophenes linked together by a bridge at one α-extremity and one binding group at the other α-extremity, is expected to improve their utility as electroactive surfactants for semiconducting nanoparticles or organic electronics.
- Edder, Carine,Frechet, Jean M. J.
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p. 1879 - 1882
(2007/10/03)
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- Rapid and efficient phosphonation of aryl halides catalysed by palladium under microwaves irradiation
-
Diethyl arylphosphonates are efficiently and rapidly prepared from aryl halides, by a palladium catalysis, performed in a Teflon autoclave under microwave radiation generated by a commercial microwave oven.
- Villemin, Didier,Jaffres, Paul-Alain,Simeon, Fabrice
-
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