17261-28-8Relevant articles and documents
Economic large-scale synthesis of o - And m -diphenylphosphinobenzoic acids
Kemme, Susanne T.,Schmidt, Yvonne,Gruenanger, Christian U.,Laungani, Andy C.,Herber, Christian,Breit, Bernhard
, p. 1924 - 1928 (2010)
An efficient and simple to perform large-scale synthesis of o- and m-diphenylphosphinobenzoic acids is presented. In a single step, both useful carboxylic acid-functionalized phosphines can be accessed starting from the same inexpensive bulk chemicals o-chlorobenzoic acid, triphenylphosphine, and sodium. In both cases the formation of the desired product is controlled by the ratio of the starting materials only. Additionally, X-ray crystallographic data are reported for both products. Georg Thieme Verlag Stuttgart New York.
Domino hydroformylation-Wittig olefination-hydrogenation
Breit, Bernhard,Zahn, Stephan K.
, p. 6171 - 6179 (2005)
Rhodium-catalyzed hydroformylation in the presence of stabilized phosphorus ylides initiates a domino hydroformylation-Wittig olefination process. When mono-substituted acceptor-stabilized phosphorus ylides were employed, a hydrogenation step succeeds the Wittig olefination to give a domino hydroformylation-Wittig olefination hydrogenation process. For the hydroformylation key step both, linear regioselective hydroformylation of terminal alkenes based on catalyst control as well as diastereoselective hydroformylation based on ortho-diphenylphosphanylbenzoate (o-DPPB)-directed active substrate control could be employed.
Synthesis and Characterization of Neutral Technetium(III)-99 and 99m Complexes with O,P-Bidentate Phosphinocarboxylate Ligands. Crystal Structure of mer-*2Me2SO
Refosco, Fiorenzo,Tisato, Francesco,Bandoli, Giuliano,Deutsch, Edward
, p. 2901 - 2908 (1993)
Reduction-substitution reactions of pertechnetate with a class of O,P-bidentate phosphinocarboxylic acid ligands HLn afforded a series of neutral and paramagnetic n3> complexes.The products have been characterized by means of elemental analysis, IR, 1H NMR, UV/VIS and FAB mass spectroscopy, and X-ray crystallography for 23>.The latter crystallizes in the monoclinic space group P21/n with Z = 4, a = 21.718(10), b = 12.954(6), c = 18.038(9) Angstroem and β = = 106.59(4) deg.The final R value was 0.061.Three deprotonated chelates surround the metal in a distorted-octahedral environment adopting a meridional configuration, and consequently there are two pairs of like donor atoms trans to one another with the remaining phosphorus atom trans to an oxygen atom.Similar reduction-substitution reactions have been performed utilizing the short-lived isotope 99mTc.The physicochemical properties of the resulting 99mTc-labelled species match very well those exhibited by the analogues prepared with the long-lived isotope 99Tc.Thus the chemical structures of n3> and n3> analogues are identical.Female Sprague-Dawley rats were injected with pre-purified n3> (n = 1, 2 or 4) and the resulting biodistributions evaluated at different times post injection.All the complexes undergo very low, but significant, brain uptake which decreases with time.
A novel convenient synthesis of aryl phosphines containing reactive functional groups
Ravindar,Hemling,Schumann,Blum
, p. 1453 - 1459 (1992)
A convenient method is described for the preparation of Ph2PC6H4COOH-2 (2) and Ph2PC6H4CHO-2 (5).
Non-classical N-metallated Pd(II) pincer complexes featuring amino acid pendant arms: Synthesis and biological activity
Churusova, Svetlana G.,Aleksanyan, Diana V.,Rybalkina, Ekaterina Yu.,Nelyubina, Yulia V.,Peregudov, Alexander S.,Klemenkova, Zinaida S.,Kozlov, Vladimir A.
, p. 70 - 82 (2018)
A series of non-classical pincer ligands with the secondary amide central unit and amino acid pendant arms was obtained from 2-diphenylphosphanyl- and 2-methylsulfanylbenzoic acids and a range of amino acid derivatives (S-methyl-L-cysteine, L-methionine, and L-histidine methyl esters). In addition, the reactions of amino acid-functionalized chloroacetamides with in situ generated Ph2PSK afforded their counterparts with an aliphatic ligand backbone. All the compounds obtained smoothly underwent direct cyclopalladation upon interaction with PdCl2(NCPh)2 under mild reaction conditions, resulting in N-metallated pincer complexes with 5,6- and 6,6-membered fused metallocycles. The realization of κ3-S,N,S-, S,N,N- and S,N,P-coordination was unambiguously confirmed based on the IR and NMR spectroscopic data. In the case of the methionine-based thiophosphorylacetamide derivative, the unexpected selectivity in the formation of one complex diastereomer was observed in solution. The solid-state structures of some of the complexes obtained were also elucidated by X-ray crystallography. The preliminary investigations on cytotoxicity of the resulting palladocycles against HCT116, MCF7, and PC3 human cancer cell lines as well as HEK293 normal cells gave some insight into the structure–activity relationships for this relatively new type of potential anticancer agents. Some of the complexes demonstrated promising cytotoxic effects.
Development of Novel Phosphino-Oxazoline Ligands and Their Application in Asymmetric Alkynlylation of Benzylic Halides
Guo, Rui,Li, Junxia,Sang, Jiale,Xiao, Haijing,Zhang, Guozhu
, (2022/03/27)
A new set of stereochemically diverse phosphino-oxazoline ligands derived from simple L-amino acids and 2-(diphenylphosphaneyl)benzoic acid were developed. Those mono anionic tridentated N,N,P-ligands promote the Cu-catalyzed enantioselective radical coupling of terminal alkynes with a broad range of benzylic halides including benzo-fused cyclic α-halides and α-silyl benzyl halides in high yield and excellent enantioselectivity under mild reaction conditions. With multi distinct sites for structural modification, a diverse pool of chiral N,N,P-ligands is readily accessed, allowing for rapid optimization of the ligand structure for a specific substrate. Notably, the enantioselective alkynlylation of benzylic halides bonds in benzo-cyclic molecules has also been realized for the first time.
The Trityl-Cation Mediated Phosphine Oxides Reduction
Landais, Yannick,Laye, Claire,Lusseau, Jonathan,Robert, Frédéric
supporting information, p. 3035 - 3043 (2021/05/10)
Reduction of phosphine oxides into the corresponding phosphines using PhSiH3 as a reducing agent and Ph3C+[B(C6F5)4]? as an initiator is described. The process is highly efficient, reducing a broad range of secondary and tertiary alkyl and arylphosphines, bearing various functional groups in generally good yields. The reaction is believed to proceed through the generation of a silyl cation, which reaction with the phosphine oxide provides a phosphonium salt, further reduced by the silane to afford the desired phosphine along with siloxanes. (Figure presented.).
ORGANIC MAGNESIUM PHOSPHIDE AND MANUFACTURING METHOD THEREOF, ORGANIC MAGNESIUM PHOSPHIDE COMPLEX AND MANUFACTURING METHOD THEREOF, AND MANUFACTURING METHOD OF ORGANIC PHOSPHORUS COMPOUND USING SAID PHOSPHIDE
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Paragraph 014-0217, (2019/08/26)
An organic magnesium phosphide expressed by Formula (1) below and an organic magnesium phosphide complex expressed by Formula (9) below are provided, and a manufacturing method of organic phosphorus compound is characterized in that the above compounds used as a reagent is reacted with an electrophile: wherein R1 and R2 are each independently an aliphatic group, heteroaliphatic group, alicyclic group, or heterocyclic group, and X is chlorine, bromine, or iodine, wherein R3 and R4 are each independently an aliphatic group, heteroaliphatic group, aromatic group, alicyclic group, or heterocyclic group, and X and Y are each independently chlorine, bromine, or iodine.
2-(diphenylphosphino)benzoic acid and synthetic method thereof
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Paragraph 0045; 0051; 0057; 0063, (2017/07/25)
The invention relates to a pesticide intermediate and a synthetic method thereof, and in particular relates to 2-(diphenylphosphino)benzoic acid and a synthetic method thereof, belonging to the technical field of chemical synthesis. The synthetic method of the 2-(diphenylphosphino)benzoic acid comprises the following steps: A, metallic sodium cracks chlorodiphenylphosphine in a refluxing organic solvent to generate sodium diphenylphosphine; B, methyl 2-chlorobenzoate is added to the sodium diphenylphosphine and reacts to generate diphenylphosphine benzoate; and C, the diphenylphosphine benzoate refluxes and reacts with 10% sodium hydroxide first to generate diphenylphosphine sodium benzoate, and then the diphenylphosphine sodium benzoate is hydrolyzed to obtain 2-(diphenylphosphino)benzoic acid. The synthetic method has the advantages of cheap and easily available raw materials, greenness, environment friendliness and no use of expensive reagents such as metallic lithium, so that the synthetic method has simple reaction conditions, few impurities, high yield, high quality and high purity of the prepared 2-(diphenylphosphino)benzoic acid, and high recovery rate of other reagents, for example, the recovery rate of organic solvents is greater than 93%, and the synthetic method can be widely used for synthesizing high-quality intermediates of pesticide.
METHOD FOR SYNTHESIS OF O-DIPHENYLPHOSPHINOBENZOIC ACID
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Page/Page column 3, (2011/04/19)
The present invention relates to a method for synthesis of o-diphenylphosphinobenzoic acid which includes the steps as follows: using chlorodiphenylphosphine as starting material, chlorodiphenylphosphine and alkali metal are added to the solvent to conduct cracking, which produces a diphenyl phosphine alkali metal salt, then o-chlorobenzoic acid salt or o-chlorobenzoic acid ester is added to conduct coupling reaction to produce diphenylphosphinobenzoic acid salt or diphenylphosphinobenzoic acid ester, o-diphenylphosphinobenzoic acid is obtained after hydrolysis. o-diphenylphosphinobenzoic acid can be prepared under atmospheric pressure at temperature above 0° C. by using the present method. The method is safe and stable to operate and can save a lot of energy, thus being suitable for large-scale production.
