104114-99-0Relevant academic research and scientific papers
Dicationic phosphonium salts: Lewis acid initiators for the Mukaiyama-aldol reaction
Barrado, Alejandro G.,Bayne, Julia M.,Johnstone, Timothy C.,Lehmann, Christian W.,Stephan, Douglas W.,Alcarazo, Manuel
, p. 16216 - 16227 (2017)
Two strategies were used to prepare dicationic phosphonium cations. The first method consists of the reaction of 1-chlorocyclopropenium salts with phosphines to obtain cyclopropenium-substituted phosphonium salts 10a-f[BF4]. Anion exchange was performed to access the corresponding [B(C6F5)4]- analogues 10a-f[B(C6F5)4], which showed much higher solubility in organic solvents. In addition, we developed a synthesis of dicationic phosphonium salts containing 2-, 3-, or 4-methylpyridinium substituents 11a-c[TfO], which were converted as well to their [B(C6F5)4]- analogues 11a-c[B(C6F5)4]. Finally, the phenoxy-substituted phosphonium salt 12[B(C6F5)4] was also prepared. All salts demonstrated remarkable stability in air as compared with their fluorinated analogues. The Lewis acidity of these salts was evaluated by means of theoretical calculations and finally, they were shown to be effective in initiating the Mukaiyama-aldol reaction.
A novel synthesis of functionalised tertiary phosphines by palladium catalysed phosphination with triarylphosphines
Kwong, Fuk Yee,Lai, Chi Wai,Tian, Yuan,Chan, Kin Shing
, p. 10285 - 10289 (2000)
The palladium catalysed Pd-aryl/P-aryl exchange was applied in the synthesis of various functionalised phosphines from their corresponding substituted aryl triflates using triarylphosphines as the phosphinating agents. This method tolerated many functional groups including ketone, aldehyde, ester, nitrile, methyl ether, pyridyl and chloride groups. (C) 2000 Elsevier Science Ltd.
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.
Fluorescent quenching agent based on cobalt metal complex, preparation method and application thereof
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Paragraph 050; 0052-0053, (2020/04/17)
The invention discloses a fluorescent quenching agent based on a cobalt metal complex, a preparation method and application thereof. Specifically, Co2(CO)8 and 1, 3-dimercaptopropane are used as the raw materials to synthesize a butterfly-shaped central body Co4(CO)6S5, which is then coordinated with pyridylphosphine ligands at different sites to synthesize the series of complexes. When used for exciting a fluorescent substance by taking a 8.0*10mol*dm zinc protoporphyrin (ZnTPP) solution as a fluorescent substance and using a 555nm light source, the fluorescent quenching agent shows an excellent quenching effect on ZnTPP, thus having important significance in researching photic driving of electron transfer and the effects in electroluminescence, dye-sensitized solar cells and catalysis.
Copper-catalyzed C–P cross-coupling of secondary phosphines with (hetero)aromatic bromide
Li, Chun-Jing,Lü, Jing,Zhang, Zhi-Xun,Zhou, Kun,Li, Yan,Qi, Guang-Hui
, p. 4547 - 4562 (2018/04/20)
A novel and convenient approach to the synthesis of various tertiary phosphines via a copper-catalyzed cross-coupling of (hetero)aromatic bromide with secondary phosphines has been developed. The reaction employs cheap copper as the catalyst, 2,6-bis(N-methylaminomethyl)pyridine (L4) as a perfect ligand and KOtBu as a base; all reactions are carried out under argon atmosphere. A variety of sterically hindered and/or functionalized substrates were found to react under these reaction conditions to provide products in good to excellent yields. Moreover, ten new tertiary phosphines were first reported in this process.
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.
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.
[NiCl2(dppp)]-catalyzed cross-coupling of aryl halides with dialkyl phosphite, diphenylphosphine oxide, and diphenylphosphine
Zhao, Yu-Long,Wu, Guo-Jie,Li, You,Gao, Lian-Xun,Han, Fu-She
supporting information; experimental part, p. 9622 - 9627 (2012/09/07)
We present a general approach to C-P bond formation through the cross-coupling of aryl halides with a dialkyl phosphite, diphenylphosphine oxide, and diphenylphosphane by using [NiCl2(dppp)] as catalyst (dppp=1,3-bis(diphenylphosphino)propane). This catalyst system displays a broad applicability that is capable of catalyzing the cross-coupling of aryl bromides, particularly a range of unreactive aryl chlorides, with various types of phosphorus substrates, such as a dialkyl phosphite, diphenylphosphine oxide, and diphenylphosphane. Consequently, the synthesis of valuable phosphonates, phosphine oxides, and phosphanes can be achieved with one catalyst system. Moreover, the reaction proceeds not only at a much lower temperature (100-120 °C) relative to the classic Arbuzov reaction (ca. 160-220 °C), but also without the need of external reductants and supporting ligands. In addition, owing to the relatively mild reaction conditions, a range of labile groups, such as ether, ester, ketone, and cyano groups, are tolerated. Finally, a brief mechanistic study revealed that by using [NiCl2(dppp)] as a catalyst, the NiII center could be readily reduced in situ to Ni0 by the phosphorus substrates due to the influence of the dppp ligand, thereby facilitating the oxidative addition of aryl halides to a Ni0 center. This step is the key to bringing the reaction into the catalytic cycle. Making bonds: C-P bonds were formed by the Ni-catalyzed cross-coupling of aryl halides and phosphorus substrates without the need of external reductants. Aryl bromides and less reactive aryl chlorides underwent smooth coupling with several different phosphorus substrates to afford phosphonates, phosphine oxides, and phosphines (see scheme; dppp=1,3-bis(diphenylphosphino)propane). Due to the mild reaction conditions, a range of labile groups, such as ether, ester, ketone, and cyano groups, are tolerated. Copyright
Nickel-catalyzed C-P cross-coupling by C-CN bond cleavage
Sun, Meng,Zhang, Hong-Yu,Han, Qi,Yang, Kuo,Yang, Shang-Dong
supporting information; experimental part, p. 9566 - 9570 (2011/10/05)
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).
Zn(ii) Robson macrocycles as templates for chelating diphosphines
Ponsico, Sergio,Gulyas, Henrik,Martinez-Belmonte, Marta,Escudero-Adan, Eduardo C.,Freixa, Zoraida,Van Leeuwen, Piet W. N. M.
experimental part, p. 10686 - 10697 (2011/12/22)
Chelating diphosphines were constructed using dinuclear Zn(ii) complexes of Robson macrocycles (Zn-RMCs) as templates. The assembly process is driven by the interaction between the metal centers (Lewis acids) with anionic and neutral Lewis base-functionalized monophosphines. The stability of the final structure depends on the geometry and the affinity of the functional groups of the ditopic phosphines and on the structure of the RMC. In the free ligand the ditopic phosphines coordinate at opposite faces of the pseudo-planar macrocycle as is shown in the molecular structure of several of the assemblies, according to X-ray diffraction. Pre-organization of the system by coordinating the phosphorus atoms to a transition metal center enforced coordination of the functional groups at the same face of the RMC. For several templated diphosphines cis-PtCl2 complexes were identified by NMR. The in situ assembled diphosphines showed a chelating effect in the rhodium catalyzed hydroformylation of 1-octene. Combination of Zn-RMC 3 and phosphine A gave the highest l/b ratio (13) in acetonitrile.
