1031-93-2Relevant articles and documents
A general synthesis of aryl phosphines by palladium catalyzed phosphination of aryl bromides using triarylphosphines
Kwong, Fuk Yee,Chan, Kin Shing
, p. 1069 - 1070 (2000)
Palladium catalyzed phosphination of substituted aryl bromides using triarylphosphines as the phosphinating agents has been developed; this method tolerates ketone, aldehyde, ester, nitrile, ether and chloride functional groups.
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 (1999)
Nickel-catalysed electrochemical cross-coupling between aryl- or heteroaryl-halides and chlorodiphenylphosphine or dichlorophenylphosphine affords tertiary phosphines in good to high yields.
Photochemical Anion-Promoted Carbon-Sulfur Cleavage Reactions of Diaryl Sulfides, Alkyl Aryl Sulfides, and Related Sulfoxides and Sulfones
Cheng, Carlos,Stock, Leon M.
, p. 2436 - 2443 (1991)
Diaryl sulfides and the related sulfoxides and sulfones react with substances such as diethyl phosphite anion, pinacolone enolate, and diphenylphosphide anion under irradiation to cleave one carbon-sulfur bond and form diethyl arylphosphonates, arylmethyl tert-butyl ketones, and aryldiphenylphosphines.Alkyl aryl sulfides and the related sulfones also experience carbon-sulfur bond cleavage under these conditions to produce arenethiols.Generally, these reactions occur in synthetically useful yields.The reactions of the anions with these sulfides, sulfoxides, and sulfones all require irradiation, but is notable that the reactions of diphenylphosphide anion occur in the visible region of the spectrum.Several lines of evidence suggest that the reaction proceeds via the familiar SRN1 pathway and that the photochemically-induced electron transfer occurs in an arene-anion complex.Thermochemical considerations dictate the cleavage direction in the anion radicals of unsymmetrical sulfides.
Copper-catalyzed synthesis of unsymmetrical triarylphosphines
Van Allen, Derek,Venkataraman
, p. 4590 - 4593 (2003)
Various triarylphosphines have been prepared by coupling diphenylphosphine with aryl iodides with catalytic amounts of CuI in the presence of either K2CO3 or CS2CO3, in good yields. This method can tolerate a variety of functional groups and does not require the use of expensive additives, or harsh reaction conditions, and is palladium free.
Application of palladium-catalyzed Pd-aryl/P-aryl exchanges: Preparation of functionalized aryl phosphines by phosphination of aryl bromides using triarylphosphines
Kwong, Fuk Yee,Lai, Chi Wai,Yu, Michael,Chan, Kin Shing
, p. 5635 - 5645 (2004)
Palladium-catalyzed Pd-aryl/P-aryl interchange reaction was applied in the synthesis of various functionalized arylphosphines. This phosphination used inexpensive, readily available and air stable triarylphosphines as the phosphinating agents. Broad functional groups were compatible including keto, aldehyde, ester, nitrile, ether, chloride, pyridyl and thiophenyl groups. Halides were found to be good promoter for the rates and yields of the reaction.
Nickel-catalyzed C-P cross-coupling by C-CN bond cleavage
Sun, Meng,Zhang, Hong-Yu,Han, Qi,Yang, Kuo,Yang, Shang-Dong
, p. 9566 - 9570 (2011)
Prosperous coupling: A nickel-catalyzed C-P cross-coupling reaction with Me3SiPPh2 by carbon-cyano bond cleavage has been developed. This method is characterized by its simplicity and wide application to the synthesis of various monophosphorus and P,N bidentate ligands (see scheme).
Ligand-free palladium catalyzed phosphorylation of aryl iodides
Nowrouzi, Najmeh,Keshtgar, Saba,Bahman Jahromi, Enayatollah
, p. 348 - 350 (2016)
A reusable ligand-free palladium catalyzed phosphorylation of aryl iodides using PdCl2/tetrabutylammonium bromide is described. Functionalized triarylphosphines were obtained in good to excellent yields in the absence of external reductants and supporting ligands.
Nickel-catalysed P-C bond formation via P-H/C-CN cross coupling reactions
Zhang, Ji-Shu,Chen, Tieqiao,Yang, Jia,Han, Li-Biao
, p. 7540 - 7542 (2015)
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
Efficient potassium hydroxide promoted P-arylation of aryl halides with diphenylphosphine
Chen, Jin,Dai, Bencai,Liu, Changchun,Shen, Zhihao,Zhou, Yang
, (2021)
A simple synthetic method of triarylphosphine compounds by KOH-promoted P-Arylation reaction of aryl halides with diphenylphosphine is presented. Notably, this transformation could smoothly proceed with high yields under transition-metal-free and mild reaction conditions. In addition, this protocol is valuable for industrial application due to the convenient operation and readily accessible aromatic halides. A possible explanation of the reaction mechanism was proposed based on the experimental data.
ARYLATION CATALYTIQUE D'ORGANOPHOSPHORES. PRODUITS DE L'ARYLATION, CATALYSEE PAR LES SELS DE NICKEL (II), DE COMPOSES DU PHOSPHORE TRICOORDINE
Cristau, Henri-Jean,Chene, Alain,Christol, Henri
, p. 283 - 296 (1980)
Analysis of the products from the nickel (II) bromide catalysed arylation of tricoordinated phosphorus compounds R2P-Z (Z = H, Cl, SR,NR2) pointed out that this arylation always takes place on phosphorus resulting at first in formation of pseudophosphonium salts.Only the aminophosphonium salts are stable under reaction conditions; the other salts undergo several transformations which can be brought together in a general reactivity scheme to account for all the side products.On regard to other heteroatoms these results point out a particular ability of phosphorus to be arylated under nickel (II) catalysis.The reaction with secondary phosphines can be applied to synthetise diarylphosphonium salts.
