1162-78-3Relevant academic research and scientific papers
Convenient and direct preparation of tertiary phosphines via nickel-catalysed cross-coupling
Ager, David J.,East, Michael B.,Eisenstadt, Amihai,Laneman, Scott A.
, p. 2359 - 2360 (1997)
Nickel-catalysed cross-coupling of aryl sulfonates and aryl halides with chlorodiphenylphosphine and a reductant directly affords tertiary phosphines, which have application in a wide variety of asymmetric catalysis.
Efficient potassium hydroxide promoted P-arylation of aryl halides with diphenylphosphine
Chen, Jin,Dai, Bencai,Liu, Changchun,Shen, Zhihao,Zhou, Yang
, (2021/06/26)
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.
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.
Ready Approach to Organophosphines from ArCl via Selective Cleavage of C-P Bonds by Sodium
Ye, Jingjing,Zhang, Jian-Qiu,Saga, Yuta,Onozawa, Shunya,Kobayashi, Shu,Sato, Kazuhiko,Fukaya, Norihisa,Han, Li-Biao
, p. 2682 - 2694 (2020/07/30)
The preparation, application, and reaction mechanism of sodium phosphide R2PNa and other alkali metal phosphides R2PM (M = Li and K) have been studied. R2PNa could be prepared, accurately and selectively, via the reactions of SD (sodium finely dispersed in mineral oil) with phosphinites R2POR′ and chlorophosphines R2PCl. R2PNa could also be prepared from triarylphosphines and diarylphosphines via the selective cleavage of C-P bonds. Na was superior to Li and K for these reactions. R2PNa reacted with a variety of ArCl to efficiently produce R2PAr. ArCl is superior to ArBr and ArI since they only gave low yields of the products. In addition, Ph2PNa is superior to Ph2PLi and Ph2PK since Ph2PLi did not produce the coupling product with PhCl, while Ph2PK only gave a low yield of the product. An electron-withdrawing group on the benzene ring of ArCl greatly accelerated the reactions with R2PNa, while an alkyl group reduced the reactivity. Vinyl chloride and alkyl chlorides RCl also reacted efficiently. While t-BuCl did not produce the corresponding product, admantyl halides could give the corresponding phosphine in high yields. A wide range of phosphines were prepared by this method from the corresponding chlorides. Unsymmetric phosphines could also be conveniently generated in one pot starting from Ph3P. Chiral phosphines were also obtained in good yields from the reactions of menthyl chlorides with R2PNa. Possible mechanistic pathways were given for the reductive cleavage of R3P by sodium generating R2PNa and the substitution reactions of R2PNa with ArCl generating R2PAr.
Differentially Substituted Phosphines via Decarbonylation of Acylphosphines
Yu, Rongrong,Chen, Xingyu,Martin, Stephen F.,Wang, Zhiqian
, p. 1808 - 1811 (2017/04/11)
A new route to phosphines was developed by a method that features a "pre-join and transform" process that proceeds via acylphosphine intermediates that may be readily prepared from carboxylic acids and disubstituted phosphines. The efficient decarbonylations of these acylphosphines using a nickel catalyst delivered the corresponding phosphines. This method shows that the carboxyl group can play a role similar to halides or triflates for introducing a substituted phosphorus atom on an aromatic ring.
Palladium-catalyzed C–P(III) bond formation reaction with acylphosphines as phosphorus source
Yu, Rongrong,Chen, Xingyu,Wang, Zhiqian
supporting information, 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.
Rhodium catalyzed hydroformylation assisted by cyclodextrins in biphasic medium: Can sulfonated naphthylphosphanes lead to active, selective and recyclable catalytic species?
Elard, Maxime,Denis, Julien,Ferreira, Michel,Bricout, Hervé,Landy, David,Tilloy, Sébastien,Monflier, Eric
, p. 47 - 54 (2015/03/30)
New sulfonated naphthylphosphanes having an average sulfonation degree around 2 have been synthetized and tested as ligand in the aqueous biphasic Rh-catalyzed hydroformylation of 1-decene assisted by randomly methylated β-cyclodextrins. All these water-soluble phosphanes associated to a rhodium precursor were able to perform aqueous hydroformylation of 1-decene. The best results in terms of catalyst recovery and recycling were obtained with sulfonated 2-naphthylphosphanes. With sulfonated 1-naphthylphosphanes, formation of low-coordinated catalytic species leading to a catalyst leaching in the organic phase was postulated. These results were rationalized by considering that sulfonated 1-naphthylphosphanes are bulkier ligands than sulfonated 2-naphthylphosphanes.
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
C-P bond-forming reactions via C-O/P-h cross-coupling catalyzed by nickel
Yang, Jia,Chen, Tieqiao,Han, Li-Biao
supporting information, p. 1782 - 1785 (2015/03/04)
The first Ni-catalyzed C-O/P-H cross-coupling producing organophosphorus compounds is disclosed. This method features wide generality in regard to both C-O and P-H compounds: for C-O compounds, the readily available alcohol derivatives of aryl, alkenyl, benzyl, and allyl are applicable, and for P-H compounds, both >PV(O)H compounds (secondary phosphine oxide, H-phosphinate, and H-phosphonate) and hydrogen phosphines (>PIIIH) can be used as the substrates. Thus, a variety of valuable C(sp2)-P and C(sp3)-P compounds can be readily obtained in good to excellent yields by this new strategy.
Convenient Formation of Triarylphosphines by Nickel-Catalyzed C-P Cross-Coupling with Aryl Chlorides
Sun, Meng,Zang, Yu-Shi,Hou, Le-Kai,Chen, Xiang-Xiang,Sun, Wei,Yang, Shang-Dong
supporting information, p. 6796 - 6801 (2016/02/18)
A convenient strategy has been developed for the preparation of various phosphine ligands in good to excellent yields through a nickel-catalyzed C-P bond-forming step. This reaction proceeded smoothly and tolerated a variety of functional groups to provide a new method for the synthesis of important phosphine ligands through the direct cleavage of a C-Cl bond. A convenient strategy has been developed for the preparation of various phosphine ligands in good to excellent yields through a nickel-catalyzed C-P bond-forming step. This reaction proceeded smoothly and tolerated a variety of functional groups to provide a new method for the synthesis of important phosphine ligands through the direct cleavage of a C-Cl bond.
