71941-98-5Relevant academic research and scientific papers
Facile phosphite to phosphonate rearrangement of a trialkanolamine-derived triphosphite promoted by triethylaluminum
Shum, Sai P.,King III, Roswell E.,Kuell, Christopher,Rodebaugh, Ronald K.,DeBellis, Anthony D.,Pastor, Stephen D.
, p. 2611 - 2623 (2007)
A facile room temperature rearrangement of a trialkanolamine-derived triphosphite, 1, to the monophosphonate 5 promoted by three equivalents of triethylaluminum is described. The diphosphonate 6 was prepared by the addition of three equivalents of triethylaluminum to the monophosphonate 5. A mechanism is suggested involving a transition state or intermediate with coordination of the trialkylaluminum to the migrating oxygen. Copyright Taylor & Francis Group, LLC.
A study of the Heck reaction in non-polar hydrocarbon solvents and in supercritical carbon dioxide
Lee, Jin-Kyun,Williamson, Rachel M.,Holmes, Andrew B.,Bush, Edward J.,McConvey, Ian F.
, p. 566 - 571 (2007)
The effects of electronic and steric properties of phosphorus ligands on Heck reactions in supercritical CO2 and non-polar hydrocarbon solvents were studied. In Heck reactions between iodobenzene and butyl acrylate, higher yields were obtained with less electron-rich phosphine ligands. This trend was also observed with the electron-poor triphenyl phosphite. A range of sterically demanding phosphites were then investigated. Biphenyl-containing phosphites 8 and 13 were found to be highly effective. In the Heck reaction between the less-reactive bromobenzene and butyl acrylate, the bulky, electron-rich tri-tert-butylphosphine ligand produced the best yield. These results emphasize the importance of both electronic and steric properties of phosphorus ligands in the Heck reaction in non-polar solvents. CSIRO 2007.
P-chirogenic diphosphazanes with axially chiral substituents and their use in rh-catalyzed asymmetric hydrogenation
Moritz, Jan-Ole,Chakrabortty, Soumyadeep,Bernd H. Mu.ller,Spannenberg, Anke,Kamer, Paul C. J.
, p. 14537 - 14544 (2020/12/29)
A convenient synthesis of enantiopure P-chirogenic diphosphazanes incorporating bulky bisphenol and 1,1′-bi-2-naphtholderived substituents via the functionalization of a readily accessible enantiopure lithium phosphinoamide with chlorophosphoridites was developed. Since the product requires no subsequent deprotection, the protocol provides an easy, convenient synthesis of P-chirogenic ligands on the gram scale. The ligands were applied in the Rh-catalyzed asymmetric hydrogenation of benchmark substrates furnishing enantiomeric excess values up to 96%.
NOVEL MONOPHOSPHITE COMPOUNDS HAVING A METHYL GROUP
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Paragraph 0128; 0129; 0130, (2016/11/17)
Novel monophosphite compounds having a methyl group, and a process for preparing these compounds, which are especially suitable for use as ligands in hydroformylation reactions.
NOVEL MONOPHOSPHITE COMPOUNDS HAVING AN ETHER GROUP
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Paragraph 0183-0184, (2016/11/17)
Novel monophosphite compounds having an ether group, and a process for preparing these compounds, which are especially suitable for use as ligands in hydroformylation reactions.
PHOSPHOROUS ACID COMPOUND, MANUFACTURING METHOD THEREFOR AND APPLICATION THEREOF
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Paragraph 0107, (2018/09/02)
PROBLEM TO BE SOLVED: To provide a novel phosphorous acid compound effective for enhancement of thermal stability and oxidation stability of organic materials and excellent in bleeding resistance. SOLUTION: There is provided a phosphorous acid compound represented by the formula (I), where A1 is a specific phosphorous acid group, A2 is a specific phenol group, A3 and A4 are each independently the specific phosphorous acid group or the specific phenol group. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
Synthesis and Reactivity of Chiral, Wide-Bite-Angle, Hybrid Diphosphorus Ligands
Czauderna, Christine Fee,Cordes, David B.,Slawin, Alexandra M. Z.,Müller, Christian,Van Der Vlugt, Jarl Ivar,Vogt, Dieter,Kamer, Paul C. J.
, p. 1797 - 1810 (2014/04/17)
Effective and modular synthetic approaches toward phosphine-phosphite ligands and phosphine-phosphonite ligands featuring a diphenyl ether backbone have been developed. The phosphine-phosphite ligands are obtained by a two-step protocol from 2-bromo-2′-methoxydiphenyl ether. The phosphine-phosphonite ligands are prepared in a four-step synthetic protocol that involves a novel, unsymmetrical diphenyl ether derived phosphine-phosphorusdiamide as key building block. Structural studies on PtII complexes with either phosphine-phosphite or phosphine-phosphonite ligands indicate strict cis coordination for these ligand systems. High-pressure NMR spectroscopy studies of Rh complexes under syngas indicate the presence of two ea isomers for Rh(H)(CO)2(PP). The existence of this mixture is further supported by high-pressure IR spectroscopy studies. In order to benchmark the activity and selectivity of these novel, wide-bite-angle, mixed-donor ligands, they were screened in Pd-catalyzed asymmetric allylic alkylation as well as Rh-catalyzed hydrogenation and hydroformylation reactions. The ligands give 100-% conversion and low-to-moderate enantioselectivity in the allylic alkylation of 1,3-diphenyl-2-propenyl acetate and cyclohexyl-2-enyl acetate with dimethyl malonate. In the hydroformylation of styrene, good conversion and regioselectivities are achieved but only moderate enantioselectivity. The ligands give good conversions in asymmetric hydrogenation of typical substrates, with good-to-excellent enantioselectivities of up to 97-% depending on the substrate. Copyright
Rhodium-catalyzed nonisomerizing hydroformylation of methyl oleate applying lactame-based phosphoramidite ligands
Benetskiy, Eduard,Luehr, Susan,Vilches-Herrera, Marcelo,Selent, Detlef,Jiao, Haijun,Domke, Lutz,Dyballa, Katrin,Franke, Robert,Boerner, Armin
, p. 2130 - 2136 (2014/07/21)
The rhodium-catalyzed hydroformylation of methyl oleate (MO) with new monodentate phosphoramidite ligands 1a-d is investigated here. The ligands are characterized by lactam rings of different size (four-to seven-membered rings). In mild conditions (synthesis gas pressure: 30 bar, 80°C), the rhodium catalysts based on the P-azetidinone phosphoramidite 1a gave within 6 h complete conversion and produced mainly methyl 9-and 10-formylstearate (MFS) with 99% chemoselectivity. In the hydrolysis test, phosphoramidite 1a was also the most stable. This was additionally confirmed by density functional theory calculations.
Phosphorus containing mixed anhydrides-their preparation, labile behaviour and potential routes to their stabilisation
Coetzee, Jacorien,Eastham, Graham R.,Slawin, Alexandra M.Z.,Cole-Hamilton, David J.
experimental part, p. 3677 - 3688 (2012/06/01)
Simple mixed anhydrides are known to pose synthetic difficulties relating to their thermal lability and ways to stabilise such mixed anhydride systems by relying on either electronic or steric effects were therefore explored. Thus, a series of acyloxyphosphines and acylphosphites derived from either propanoic acid or phenylacetic acid were prepared and their in solution stability assessed. These compounds were, where stability allowed, fully characterised using standard analytical techniques. NMR studies, in particular, unearthed interesting coupling behaviour for a number of the acyloxyphosphines and acylphosphites as well as their rearrangement products which could be linked to their chiral nature. Furthermore, the crystal structures for three of the prepared mixed anhydrides were determined using X-ray crystallography and are reported herein.
Carbonylation Method by Adding Secondary Sterically Hindered Amines
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Page/Page column 13, (2008/12/07)
The invention relates to a process for reaction of a carbonylatable compound using a metal complex catalyst comprising a metal of transition group VIII and an organophosphorus ligand and in the presence of a stabilizer based on a sterically hindered secondary amine.
