1486-28-8Relevant articles and documents
Choukroun, Robert,Dahan, Francoise,Gervais, Daniele
, p. C33 - C36 (1984)
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Seyferth,Burlitch
, p. 2463 (1963)
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Palladium-Catalyzed Cleavage of P-C Bonds In Quaternary Phosphonium Salts and Its Applications to Organic Synthesis
Sakamoto, Masato,Shimizu, Isao,Yamamoto, Akio
, p. 1101 - 1102 (1995)
Phosphonium salts, PPh4I and PMePh3I, oxidatively add to Pd(methyl acrylate)(PMePh2)2 to give trans- in moderate yields with cleavage of the P-phenyl bond.Conversely thermolysis of trans-PdPhIL2(L = PMePh2 and PPh3) reductively eliminates PMePh3I and PPh4I, respectively.Application of the P-C bond cleavage process in phosphonium salts to olefination, carbonylation and hydrogenation reactions has been explored.
Dimethylsulfonium methylide in methylation of silylphosphines
Veits,Chuchuryukin,Neganova
, p. 1790 - 1792 (2002)
Selective monodesilylation of bissilylated alkyl- or arylphosphines under the action of dimethylsulfonium methylide and the subsequent methylation of the resulting silyl phosphides with the sulfonium salt offers a convenient route to difficultly accessible monosilylated secondary methylalkyl(aryl)phosphines.
Poli, Rinaldo,Owens, Beth E.,Krueger, Steven T.,Rheingold, Arnold L.
, p. 2301 - 2312 (1992)
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.).
A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics
García-Domínguez, Andrés,Gonzalez, Jorge A.,Leach, Andrew G.,Lloyd-Jones, Guy C.,Nichol, Gary S.,Taylor, Nicholas P.
supporting information, (2022/01/04)
The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.
Reductive conversion of phosphoryl P(O) compounds to trivalent organophosphines R3P
Zhang, Jian-Qiu,Han, Li-Biao
, (2021/02/20)
By introducing trimethylsilyl chloride (TMSCl), the pentavalent phosphoryl P(V) compounds such as triphenylphosphine oxides, secondary phosphine oxides etc., were readily converted to the corresponding R2P(OTMS) intermediates, that can further react efficiently with an electrophile R'X or with a nucleophile R'Li to produce the corresponding trivalent phosphines R2PR’. Chiral phosphines could also be obtained stereospecifically by this strategy.