739-58-2Relevant articles and documents
[4-(N,N-dimethylamino)phenyl]diphenylphosphine oxide and its partial oxides: An isomorphous crystal series
Lynch, Daniel E.,Smith, Graham,Byriel, Karl A.,Kennard, Colin H.L.
, p. 1135 - 1139 (2003)
The title compound [4-(N,N-dimethylamino)phenyl]diphenylphosphine oxide (1) has been synthesized and its single-crystal X-ray structure determined. The structures of two 'partial' oxides of the parent compound, (2) and (3) (50% and 25% oxidized), isolated from the intermediate phosphine reaction product have also been determined, yielding an unusual isomorphous crystal series. An apparent P-O bond shortening with increasing oxidation is also observed across the series (1)-(3) (1.480(4), 1.351(4), 1.280(4) A respectively) and is considered an artifact of the structure refinement. The packing in the crystals shows primary one-dimensional chains with weak head-to-tail associations between the oxide oxygen (three-centre) and two hydrogen atoms from separate methyl groups of the N-substituted amine (range C-H...O 3.115(4)-3.356(8) A), extended into a sheet structure by peripheral inter-chain C-H (aromatic)...O (oxide) associations.
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.).
Chemoselective Reduction of Phosphine Oxides by 1,3-Diphenyl-Disiloxane
Buonomo, Joseph A.,Eiden, Carter G.,Aldrich, Courtney C.
, p. 14434 - 14438 (2017/10/23)
Reduction of phosphine oxides to the corresponding phosphines represents the most straightforward method to prepare these valuable reagents. However, existing methods to reduce phosphine oxides suffer from inadequate chemoselectivity due to the strength of the P=O bond and/or poor atom economy. Herein, we report the discovery of the most powerful chemoselective reductant for this transformation to date, 1,3-diphenyl-disiloxane (DPDS). Additive-free DPDS selectively reduces both secondary and tertiary phosphine oxides with retention of configuration even in the presence of aldehyde, nitro, ester, α,β-unsaturated carbonyls, azocarboxylates, and cyano functional groups. Arrhenius analysis indicates that the activation barrier for reduction by DPDS is significantly lower than any previously calculated silane reduction system. Inclusion of a catalytic Br?nsted acid further reduced the activation barrier and led to the first silane-mediated reduction of acyclic phosphine oxides at room temperature.
A preparation method of compound phosphine benzene apperception (by machine translation)
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Paragraph 0090; 0091; 0092; 0093, (2016/11/14)
The invention relates to a method for preparing phosphine benzene apperception compound, the bromine compound is made with the magnesium reaction of Grignard reagent, then using four (triphenylphosphine) palladium-catalyzed bromophenylacetic compound phosphine chlorination reaction with the Grignard reagent. The specific method is, under the protection of inert gas, the bromo compound is made with the magnesium chips and organic solvent Grignard reagent, reflux 2 the [...] 10 hours; joined four at room temperature (triphenylphosphine) palladium, stirring 10 minutes to 3 hours, chlorinated room temperature instillment phosphine composition, reflux reaction the 1 [...] 10 hours; in the ice water bath in the fluid adds by drops full and weak acid to the reaction under weak alkali salt-water solution, liquid, organic phase exsolution, alcohol solvent crystallization, filtering to obtain compound phosphine benzene. The preparation method of this invention not only greatly improves manufacturing yield, and after treatment is simple, the process of repeated washing with ammonia water, the manufacturing process is simplified, is beneficial for large-scale industrial production. (by machine translation)
Nickel-catalysed P-C bond formation via P-H/C-CN cross coupling reactions
Zhang, Ji-Shu,Chen, Tieqiao,Yang, Jia,Han, Li-Biao
supporting information, p. 7540 - 7542 (2015/05/04)
Nickel-catalysed P-H/C-CN cross coupling reactions take place efficiently under mild reaction conditions affording the corresponding sp2C-P bonds. This transformation provides a convenient method for the preparation of arylphosphines and arylphosphine oxides from the readily available P-H compounds and arylnitriles. This journal is
Electrosynthesis of triorganylphosphines from organic halides and chlorophosphines, catalyzed by nickel complexes
Budnikova,Kargin,Sinyashin
, p. 524 - 528 (2007/10/03)
The possibility of cross coupling of organic halides and chlorophosphines under the action of electrochemically generated Ni(0) complexes of 2,2′-bipy is shown. The final triorganylphosphines are formed by several pathways, including reaction of the σ complex of ArNiX with chlorophosphine and electron transfer-induced reductive elimination of Ph2PArNiX, leading to the cross-coupling product.
Nickel-catalysed electrochemical coupling between mono- or di-chlorophenylphosphines and aryl or heteroaryl halides
Budnikova, Yulia,Kargin, Yuri,Nedelec, Jean-Yves,Perichon, Jacques
, p. 63 - 66 (2007/10/03)
Nickel-catalysed electrochemical cross-coupling between aryl- or heteroaryl-halides and chlorodiphenylphosphine or dichlorophenylphosphine affords tertiary phosphines in good to high yields.
Syntheses and Spectroscopic Investigations of Substituted cis- and trans-Dichlorobis(triphenylphospane)platinum(II) Compounds
Brune, Hans Albert,Falck, Manfred,Hemmer, Reinhard,Schmidtberg, Guenter,Alt, Helmut G.
, p. 2791 - 2802 (2007/10/02)
Compounds of the type cis- and trans-dichlorobis(triphenylphosphane)platinum(II) (3) with substituents of different electronic character in the phenyl rings bonded to phosphorus have been synthesized.The coupling constants 1J and the chloro-platinum valence vibrational frequencies are demonstrated to be criteria for unambiguous discrimination between cis- and trans-configurations at platinum; a linear correlation exists between the sum of the ?-constants of the sustituents at the triphenylphosphane and the coupling constants 1J.
PHOSPHORORGANISCHE VERBINDUNGEN 102. TERTIAERE PHOSPHINE MIT o-DIALKYLAMINOPHENYL- UND ORTHO-DIALKYLAMINOBENZYLGRUPPEN
Horner, L.,Simons, G.
, p. 165 - 176 (2007/10/02)
N,N-dialkylarylamines and N,N-dialkylbenzylamines are lithiated with n-butyllithium (n-BuLi) under the assistance of tetramethylethylenediamine (TMEDA) in the ortho-position.According the Eqs. (1) and (4) triarylphosphines (30-50percent) are obtained. 1-(N,N-dimethylamino)-naphthalene and N,N-dimethyl-1-(1-naphthyl)-ethylamine 18 are lithiated in the 8-position.In N,N-dimethyl-1-(2-naphthyl)-ethylamine 19 the 1- and 3-position is lithiated in nearly equal amount.Experiments to introduce lithium twice into the model compounds 28-30 are without success.
