13885-03-5Relevant academic research and scientific papers
Palladium-Catalyzed C-P(III) Bond Formation by Coupling ArBr/ArOTf with Acylphosphines
Chen, Xingyu,Wu, Hongyu,Yu, Rongrong,Zhu, Hong,Wang, Zhiqian
, p. 8987 - 8996 (2021/06/30)
Palladium-catalyzed C-P bond formation reaction of ArBr/ArOTf using acylphosphines as differential phosphination reagents is reported. The acylphosphines show practicable reactivity with ArBr and ArOTf as the phosphination reagents, though they are inert to the air and moisture. The reaction affords trivalent phosphines directly in good yields with a broad substrate scope and functional group tolerance. This reaction discloses the acylphosphines' capability as new phosphorus sources for the direct synthesis of trivalent phosphines.
Diverse C-P Cross-Couplings of Arylsulfonium Salts with Diarylphosphines via Selective C-S Bond Cleavage
Ye, Yun,Zhu, Jie,Huang, Yinhua
, p. 2386 - 2391 (2021/04/05)
Diverse C-P cross-couplings of arylthianthrenium salts with diarylphosphines producing various triarylphosphines via highly selective C-S bond cleavage are reported. In the absence of catalyst, the reaction of arylthianthrenium salts with diarylphosphines undergoes phosphinative ring opening exclusively via the cleavage of an endocyclic C-S bond of a thianthrene skeleton. The use of a palladacycle catalyst under otherwise the same conditions enables the phosphination via the cleavage of an exocyclic C-S bond with significantly higher speed.
Preparing method of triarylphosphine compound
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Paragraph 0040; 0041; 0042; 0043; 0044, (2019/07/16)
The invention belongs to the technical field of medicine and natural compound chemical intermediates and relevant chemistry, and provides a preparing method of a triarylphosphine compound. According to the preparing method, a diphenylphosphine compound and aryl halide serve as raw materials, participation of transition metal catalysts is not needed, and the triarylphosphine compound is constructedin one step under the heating condition. The preparing method has the advantages that according to the reaction, the metal or non-metal catalysts are not needed for catalytic reactions, the triarylphosphine compound is clean and free of pollution, the reaction condition is mild, the operation and aftertreatment are simple, and the substrate compatibility is good.
A practical synthesis of unsymmetrical triarylphosphines by heterogeneous palladium(0)-catalyzed cross-coupling of aryl iodides with diphenylphosphine
Xu, Zhaotao,Wang, Pingping,Chen, Qiurong,Cai, Mingzhong
, p. 50 - 58 (2018/04/23)
The heterogeneous cross-coupling reaction of aryl iodides with diphenylphosphine was achieved in DMAc at 130 °C in the presence of 1.0 mol% of MCM-41-supported tridentate nitrogen palladium(0) complex [MCM-41-3N-Pd(0)] with KOAc as base, yielding a variety of unsymmetrical triarylphosphines in good to excellent yields. The turnover frequency (TOF) of the catalyst can reach 30.67 h?1. This new heterogeneous palladium(0) catalyst could easily be prepared by a simple procedure from commercially readily available reagents, and exhibited the same catalytic activity as homogeneous Pd(OAc)2 or Pd(PPh3)4, and could be recovered by filtration of the reaction solution and recycled at least seven times without significant loss of catalytic activity.
An efficient heterogeneous cross-coupling of aryl iodides with diphenylphosphine catalyzed by copper (I) immobilized in MCM-41
Fang, Zhiqiang,Cai, Mingzhong,Lin, Yang,Zhao, Hong
, (2018/07/31)
The heterogeneous cross-coupling reaction of aryl iodides with diphenylphosphine was achieved in toluene at 115?°C in the presence of 10?mol% of phenanthroline-functionalized MCM-41-supported copper (I) complex (Phen-MCM-41-CuI) with Cs2CO3 as base, yielding various unsymmetric triarylphosphines in good to excellent yields. This protocol can tolerate a wide range of functional groups and does not need the use of expensive additives or harsh reaction conditions. This heterogeneous Cu (I) catalyst exhibited the same catalytic activity as homogeneous CuI/Phen system, and could easily be recovered by a simple filtration of the reaction solution and recycled up to seven times without significant loss of activity.
Palladium-catalyzed C–P(III) bond formation reaction with acylphosphines as phosphorus source
Yu, Rongrong,Chen, Xingyu,Wang, Zhiqian
, p. 3404 - 3406 (2016/07/11)
Palladium-catalyzed C–P(III) bond formation reaction employing acylphosphines as the phosphorus source was developed. Under the optimized conditions, acylphosphines could react with aryl halides directly affording trivalent phosphines in up to 94% yield.
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
An examination of the effects of borate group proximity on phosphine donor power in anionic (phosphino)tetraphenylborate ligands
Tassone, Joseph P.,Mawhinney, Robert C.,Spivak, Gregory J.
, p. 153 - 156 (2015/02/19)
The ligand electron-donating abilities are compared among a series of monodentate, anionic (phosphino)tetraphenylborate phosphines [Ph4P][Ph2P-R-C6H4BPh3] (R = -C6H4-, -CH2-, -CH2CH2- or none), and their neutral counterparts Ph2PR (R = biphenyl, -CH2Ph, -CH2CH2Ph or Ph). Among the anionic ligands, the position of the tetraphenylborate group relative to the diphenylphosphino donor moiety was systematically varied in an effort to examine how its proximity impacts donor power. The donor power was determined by measuring the 31P-77Se coupling constant for the corresponding selenide of each phosphine ligand via 31P NMR spectroscopy. The anionic ligands yield lower 31P-77Se coupling constants than those measured for their respective neutral counterparts. Moreover, the 31P-77Se coupling constants among the anionic ligands increase when the tetraphenylborate group is positioned further from the phosphorus centre.
Properties and catalytic activities of new easily-made amphiphilic phosphanes for aqueous organometallic catalysis
Ferreira, Michel,Bricout, Herve,Azaroual, Nathalie,Gaillard, Cedric,Landy, David,Tilloy, Sebastien,Monflier, Eric
experimental part, p. 1193 - 1203 (2010/07/07)
Mono- and disulfonated amphiphilic versions of triphenylphosphane (PPh 3) and cyclohexyl(phenyl)phosphane were easily synthesized from commercial reagents and sulfuric acid. The behaviour of these phosphanes in solution was investigated by surf
