- Cyclooctene epoxidation with H2O2 and single crystal X-ray determined crystal structures of new molybdenum and tungsten catalysts bearing the hydrophilic ligand hydroxymethyldiphenylphosphine oxide
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The dioxo molybdenum and tungsten complexes MoO2Cl2(OPPh2CH2OH)2 and WO2Cl2(OPPh2CH2OH)2 have been synthesized and characterized by FT-IR, 1
- Feng, Linsheng,Urnezius, Eugenijus,Luck, Rudy L.
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Read Online
- Synthesis and evaluation of photophysical and electrochemical properties of vinyl chalcogenide derivatives of phenothiazines
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The Wittig-Horner mediated syntheses of phenothiazines carrying vinylsulfide and vinylselenide motifs attached to the aromatic ring(s) or connected to the central nitrogen atom of the heterocycle, and the subsequent study of their photophysical and electr
- Dilelio, Marina Cardoso,Iglesias, Bernardo Almeida,Kaufman, Teodoro S.,Silveira, Claudio C.
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- C-Alkyl-bis-phosphoryl chelating systems for the potential recovery of strategic metals
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Methylene-bis-phosphonic acid and derivatives are used as complexing agents, diagnostics, therapeutics and show interesting virustatic properties. We describe the syntheses of mono- and di-substituted bisphosphonates and mono- and disubstituted diethyl ((diphenylphosphoryl)methyl)phosphonate as possible chelating systems for the recovery of strategic metals.
- Babouri, Rachida,Halidou Dougourikoye, Abdoul Razak,Ilagouma, Amadou TidJani,Pirat, Jean-Luc,Virieux, David,Volle, Jean-No?l
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- C-2 auxiliaries for stereoselective glycosylation based on common additive functional groups
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The stereoselective introduction of the glycosidic bond is one of the main challenges in chemical oligosaccharide synthesis. Stereoselective glycosylation can be achieved using neighbouring group participation of a C-2 auxiliary or using additives, for example. Both methods aim to generate a defined reactive intermediate that reacts in a stereoselective manner with alcohol nucleophiles. This inspired us to develop new C-2 auxiliaries based on commonly used additive functionalities such as ethers, phosphine oxides and tertiary amides. Good 1,2-trans-selectivity was observed for the phosphine oxide and amide-based auxiliaries expanding the toolbox with new auxiliaries for stereoselective glycosylation reactions.
- Boltje, Thomas J.,De Kleijne, Frank F. J.,Moons, Sam J.,White, Paul B.
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p. 1165 - 1184
(2020/02/22)
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- Reduction of Tertiary Phosphine Oxides by BH 3 Assisted by Neighboring Activating Groups
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Tertiary sulfanylphosphine and aminoalkylphosphine oxides can be easily converted into the corresponding tertiary sulfanylphosphine- and aminoalkylphosphine-boranes, respectively, through the facile P=O bond reduction by borane complexes. The easy reduction of the strong P=O bond by BH 3, a mild reducing agent, has been achieved through an intramolecular P=O - B complexation directed by proximal SH or NH activating groups located at the α- or β-position to the P=O bond. A generalized reduction mechanism has been proposed.
- Sowa, Sylwia,Stankevi?, Marek,Flis, Anna,Pietrusiewicz, K. Micha?
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p. 2106 - 2118
(2018/02/28)
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- A Photo-Triggered Traceless Staudinger–Bertozzi Ligation Reaction
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The use of light to control the course of a chemical/biochemical reaction is an attractive idea because of its ease of administration with high precision and fine spatial resolution. Staudinger ligation is one of the commonly adopted conjugation processes that involve a spontaneous reaction between azides and arylphosphines to form iminophosphoranes, which further hydrolyze to give stable amides. We designed an anthracenylmethyl diphenylphosphinothioester (1) that showed promising Staudinger ligation reactivity upon photo-excitation. Broadband photolysis at 360–400 nm in aqueous organic solvents induced heterolytic cleavage of its anthracenylmethyl–phosphorus bond, releasing a diphenylphosphinothioester (2) as an efficient traceless Staudinger–Bertozzi ligation reagent. The quantum yield of such a photo-induced heterolytic bond-cleavage at the optimal wavelength of photolysis (376 nm) at room temperature is ≥0.07. This work demonstrated the feasibility of photocaging arylphosphines to realize the photo-triggering of the Staudinger ligation reaction.
- Hu, Peng,Feng, Tianshi,Yeung, Chi-Chung,Koo, Chi-Kin,Lau, Kai-Chung,Lam, Michael H. W.
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p. 11537 - 11542
(2016/08/05)
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- Toward New Organometallic Architectures: Synthesis of Carbene-Centered Rhodium and Palladium Bisphosphine Complexes. Stability and Reactivity of [PCBImPRh(L)][PF6] Pincers
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In this article, we report the synthesis of a tridentate carbene-centered bisphosphine ligand precursor and its complexes. The developed four-step synthetic strategy of a new PCBImP pincer ligand represents the derivatization of benzimidazole i
- Plikhta, Andriy,P?thig, Alexander,Herdtweck, Eberhardt,Rieger, Bernhard
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supporting information
p. 9517 - 9528
(2015/10/12)
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- Synthesis and photophysical characterization of novel π-conjugated vinyl sulfides
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The synthesis and photophysical properties of a series of π-conjugated vinyl sulfides are described. These compounds exhibited their absorption maxima in the range of 350-366 nm, while the emission spectra displayed peaks in the zone of 421-441 nm; both o
- Bassaco, Mariana M.,Mon?alves, Matias,Rinaldi, Francieli,Kaufman, Teodoro S.,Silveira, Claudio C.
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- Diarylphosphine- and dialkylphosphine-containing compounds, processes of preparing same and uses thereof as tridentate ligands
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A novel process of preparing tridentate ligands containing one or more of a diarylphosphine and/or dialkylphosphine electron donating groups are disclosed. Use of this process for preparing a combinatorial library of such tridentate ligands and of organometallic complexes containing same is also disclosed. Further disclosed are novel diarylphosphine-containing and dialkylphosphine-containing compounds that can serve as tridentate ligands (e.g., pincer ligands), combinatorial libraries of such tridentate ligands, organometallic complexes containing these ligands (e.g., pincer complexes), and combinatorial libraries of such complexes. Methods utilizing these libraries for screening for candidate organometallic catalysts are also disclosed. Novel precursor molecules useful for preparing the tridentate ligands and processes of preparing same are also disclosed.
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Page/Page column 35-36
(2012/12/13)
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- Synthesis of cyclopropane-containing phosphorus compounds by radical coupling of butenylindium with iodo phosphorus compounds
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The radical coupling of α- or β-iodo phosphorus compounds such as iodo phosphonate, iodo phosphane oxide, and iodo phosphonothioate with butenylindium species, prepared by transmetalation between a (cyclopropylmethyl)stannane and InBr3, afforded the corresponding cyclopropylmethylated products. The radical reaction was initiated by the radical species generated from butenylindium assisted by a small amount of oxygen. Butenylindium works not only as a cyclopropylmethylating reagent, but also as a radical initiator. For successful coupling, a tin/indium transmetalation was used, where it was important for the tin halide by-product to be inert to the reaction system. In addition, the transmetalation of a (cyclopropylmethyl)stannane and InBr3 provided the dibutenylindium bromide as a single product, which smoothly coupled with the unstable phosphonyl radical species from the iodo phosphorus compound. A photochemical method (UV irradiation) was also applied and accelerated the coupling reaction. The cyclopropylmethylated phosphonate produced was a good intermediate in the Horner-Wadsworth-Emmons reaction and gave functionalized olefins bearing the cyclopropane moiety. Copyright
- Kiyokawa, Kensuke,Suzuki, Itaru,Yasuda, Makoto,Baba, Akio
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supporting information; experimental part
p. 2163 - 2171
(2011/05/16)
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- Pincer click ligands
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(Chemical Equation Presented) It all clicks into place: The use of "click chemistry" has been found to be highly advantageous for the selective and rapid combinatorial synthesis of a family of pincer-type ligands from relatively simple building blocks (se
- Schuster, Elaine M.,Botoshansky, Mark,Gandelman, Mark
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supporting information; experimental part
p. 4555 - 4558
(2009/02/08)
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- Thermolyses of α-phosphorylmethyl tetrazolyl sulfoxides in the presence of 2,3-dimethyl-1,3-butadiene and their reactions with several amines
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We have synthesized α-(phosphoryl)methyl tetrazolyl sulfoxides and examined the reactivities in the thermolyses and in the presence of several amines, such as aniline, benzylamine, piperidine, pyrrolidine, and morpholine. Thermolyses of the derivatives in the presence of 2,3-dimethyl-1,3-butadiene afforded 2-phosphoryl substituted 4,5-dimethyl-3,6-dihydro-2H-thiopyran S-oxide. In addition, novel phosphinecarbothioamides were obtained in the reaction of the derivatives with amines.
- Morita, Hiroyuki,Tashiro, Shintaro,Takeda, Masahiro,Fujimori, Ken,Yamada, Nobuhiko,Chanmiya Sheikh,Kawaguchi, Hiroyuki
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p. 3589 - 3595
(2008/09/20)
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- Preparation and reactivity of chalcogenyl phosphonates and phosphane oxides
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The preparation of new bis[(diphenylphosphinoyl)methyl] sulfides, selenides, and tellurides is described by the reaction of (diphenylphosphinoyl) methyl p-toluenesulfonate with sodium chalcogenides. The title compounds are subjected to Horner-Wittig-type
- Silveira, Claudio C.,Rinaldi, Francieli,Guadagnin, Rafael C.
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p. 4935 - 4939
(2008/03/14)
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- The synthesis of benzylphosphine oxidesvia vicarious nucleophilic substitution and alkenes via VNS-Horner-Wittig reactions
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A range of substituted nitrobenzenes react with the anion of (chloromethyl)diphenylphosphinoyl oxide to give the substituted nitrobenzyldiphenylphosphine oxide by vicarious nucleophilic substitution. The novel stereoselective synthesis of E-stilbenes via a one-pot vicarious nucleophilic substitution-Horner-Wittig reaction is described.
- Lawrence, Nicholas J.,Liddle, John,Jackson, David
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p. 2260 - 2267
(2007/10/03)
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- Phosphorus-containing podands: XV. Synthesis of bis(diphenylphosphinoylmethyl) ethers of oligoethylene glycols and selectivity of their complex formation with alkali metal cations in a low-polarity solvent
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An improved procedure for preparing bis(diphenylphosphinoylmethyl) ethers of oligoethelene glycols of the general formula Ph2P(O)CH2O(CH2CH2O)nCH 2P(O)Ph2 (n = 0-6) is developed, and the stability constants of their alkali cation complexes in the THF-CHCl3 system at 25°C were determined by conductometry.
- Tsvetkov,Evreinov,Bondarenko,Safronova
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p. 1039 - 1046
(2007/10/03)
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- The effect of the phosphoryl group on the rate and mechanism of SN-substitution at the saturated carbon atoms
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The reactivity of diarylphosphine oxides RR'P(O)CH2X with p-O2NC6H4ONa in DMF have been studied.The reaction rate increases with the electrodrawing properties of the substituents on R and R' in the following way: p-Me2NC6H4 2 reaction rate of diphenylphosphine oxides has been investigated.The reactivity increases as follows Cl I Br OTs.A reaction mechanism is suggested.
- Tsvetkov, E. N.,Tkachenko, S. E.,Yarkevich, A. N.
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p. 339 - 341
(2007/10/02)
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- SYNTHESIS OF THE E- AND Z-ISOMERS OF THE POTENT MUTAGEN (S)-FECAPENTAENE-12 BY THE HORNER-WITTIG REACTION
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A synthesis of the E- and Z-isomers of optically pure (S)-fecapentaene-12 is described.The method is beased on the chromatographic separation of diastereomeric adducts, formed as intermediates in the Horner-Wittig reaction of an all-trans undecatetraenal,
- Wit, P.P de,van der Steeg, M.,van der Gen, A.
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p. 307 - 308
(2007/10/02)
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- A CONVENIENT SYNTHESIS OF FECAPENTAENE-12 BY THE HORNER-WITTIG REACTION
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A synthesis of racemic fecapentaene-12 and other glyceryl enol ethers has been developed based on the Horner-Wittig reaction.Coupling of the anion of the glyceryl substituted phosphine oxide 7 with unsaturated aldehydes 9a-c provided, after treatment with base, the silyl protected glyceryl enol ethers 11a-c.The silyl groups were easily removed and mixtures of E and Z isomers of glyceryl enol ethers 12a-c were obtained.The isomers could be separated upon washing with ether/hexane.
- Wit, P. P. de,Schaik, T. A. M. van,Gen, A. van der
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p. 369 - 370
(2007/10/02)
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