13406-28-5

Usage

Uses

Used in Transition Metal Catalysis:
Diphenyl[4-(trifluoromethyl)phenyl]phosphine is used as a ligand in transition metal catalysis for its ability to form stable complexes with transition metals. This enhances the catalytic activity and selectivity of the metal center, facilitating various chemical reactions.
Used in Organic Synthesis:
Diphenyl[4-(trifluoromethyl)phenyl]phosphine is used as a reagent in organic synthesis for its unique reactivity and ability to form stable intermediates. This allows for the efficient construction of complex organic molecules and the development of novel synthetic routes.
Used in the Study of Phosphine Compounds:
Diphenyl[4-(trifluoromethyl)phenyl]phosphine is used as a model compound to study the properties and behavior of phosphine compounds. Its unique structure allows researchers to gain insights into the reactivity, stability, and potential applications of phosphine derivatives in various chemical processes.

Upstream product

• 402-43-7 p-trifluoromethylphenyl bromide 
• 1079-66-9 chloro-diphenylphosphine 
• 455-13-0 4-Iodobenzotrifluoride 
• 1213-51-0 (trimethylstannyl)diphenylphosphine 
• 40841-62-1 (diphenylphosphino)(p-tolyl)methanone 
• 829-85-6 diphenylphosphane 
• 146397-87-7 p-(trifluoromethyl)phenyl trifluoromethanesulfonate 
• 98-56-6 4-chlorobenzotrifluoride 
• 4376-01-6 sodium diphenylphosphide 
• 1031-93-2 diphenyl(p-tolyl)phosphine 
• 7650-91-1 benzyldiphenylphosphane 
• 6372-40-3 isopropyldiphenylphosphine 
• 15475-27-1 potassium diphenylphosphine 
• 603-35-0 triphenylphosphine 

Downstream Products

• 13406-19-4 4-Nitro-N--anilin 
• 13406-24-1 4-Trifluormethyl-N--anilin 
• 436149-53-0 trans-[RhCl(CO)(PPh₂(2-C₆H₄CF₃))2] 
• 941294-01-5 PtCl₂(4-(trifluoromethylphenyl)diphenylphosphine)2 
• 60271-68-3 2-(4-{[diphenyl-(4-trifluoromethyl-phenyl)-phosphonio]-methyl}-styryl)-3-methyl-benzothiazolium; bis-bromide 
• 13406-17-2 N--anilin 
• 60271-51-4 [4-(2-benzothiazol-2-yl-vinyl)-benzyl]-diphenyl-(4-trifluoromethyl-phenyl)-phosphonium; bromide 

Relevant academic research and scientific papers

Nickel-catalyzed reductive coupling of chlorodiphenylphosphine with aryl bromides into functionalized triarylphosphines

Functionalized triarylphosphines are obtained with good yields in a one-step reaction of an equimolar mixture of chlorodiphenylphosphine and an aromatic bromide in NMP or DMF at 110°C in the presence of zinc dust and a catalytic amount of NiBr2

Strong π-acceptor sulfonated phosphines in biphasic rhodium-catalyzed hydroformylation of polar alkenes

A new series of sulfonated triarylphosphines with a strong π-acceptor character were synthesized by direct sulfonation of trifluoromethylated neutral phosphines. Due to the deactivating character of the trifluoromethyl group, high oleum concentration and the use of boric acid to prevent phosphine oxidation were required for the sulfonation step. The new sulfonated phosphines are water-soluble and more inert toward oxidation than classical sulfonated phosphines. The use of these trifluoromethylated and sulfonated phosphines as ligands in the biphasic hydroformylation of vinyl acetate and allyl cyanide increases the rate of the reaction up to 4 times, compared to the results obtained with the non-trifluoromethylated counterparts, TPPMS, TPPDS and TPPTS. Moreover, it is possible to recycle the catalyst without a significant loss of the system activity.

Palladium-Catalyzed C-P(III) Bond Formation by Coupling ArBr/ArOTf with Acylphosphines

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.

Systematic Study of the Stereoelectronic Properties of Trifluoromethylated Triarylphosphines and the Correlation of their Behaviour as Ligands in the Rh-Catalysed Hydroformylation

The stereoelectronic properties of a series of trifluoromethylated aromatic phosphines have been studied using different approaches. The σ-donating capability has been evaluated by nuclear magnetic resonance (NMR) spectroscopy of the selenide derivatives and the protonated form of the different trifluoromethylated phosphines. The coupling constants between phosphorous and selenium (1JSeP) and phosphorous and hydrogen (1JHP) can be predicted by empirical equations and correlate the basicity of the phosphines with the number and relative position of trifluoromethyl groups. In contrast, the π-acceptor character of the ligands has been evaluated by measuring the frequency of the CO vibration in the infrared (IR) spectra of the corresponding Vaska type iridium complexes ([IrCl(CO)(PAr3)2], PAr3=triarylphosphine). Moreover, the correlation between the electronic properties and the performance of these phosphines as ligands in the rhodium-catalysed hydroformylation of 1-octene has been established. Phosphines with the lowest basicity, that are those with the highest number of trifluoromethyl groups, gave rise to more active catalytic systems.

Versatile Visible-Light-Driven Synthesis of Asymmetrical Phosphines and Phosphonium Salts

Asymmetrically substituted tertiary phosphines and quaternary phosphonium salts are used extensively in applications throughout industry and academia. Despite their significance, classical methods to synthesize such compounds often demand either harsh reaction conditions, prefunctionalization of starting materials, highly sensitive organometallic reagents, or expensive transition-metal catalysts. Mild, practical methods thus remain elusive, despite being of great current interest. Herein, we describe a visible-light-driven method to form these products from secondary and primary phosphines. Using an inexpensive organic photocatalyst and blue-light irradiation, arylphosphines can be both alkylated and arylated using commercially available organohalides. In addition, the same organocatalyst can be used to transform white phosphorus (P4) directly into symmetrical aryl phosphines and phosphonium salts in a single reaction step, which has previously only been possible using precious metal catalysis.

Ready Approach to Organophosphines from ArCl via Selective Cleavage of C-P Bonds by Sodium

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.

Chemoselective Reduction of Phosphine Oxides by 1,3-Diphenyl-Disiloxane

Reduction of phosphine oxides to the corresponding phosphines represents the most straightforward method to prepare these valuable reagents. However, existing methods to reduce phosphine oxides suffer from inadequate chemoselectivity due to the strength of the P=O bond and/or poor atom economy. Herein, we report the discovery of the most powerful chemoselective reductant for this transformation to date, 1,3-diphenyl-disiloxane (DPDS). Additive-free DPDS selectively reduces both secondary and tertiary phosphine oxides with retention of configuration even in the presence of aldehyde, nitro, ester, α,β-unsaturated carbonyls, azocarboxylates, and cyano functional groups. Arrhenius analysis indicates that the activation barrier for reduction by DPDS is significantly lower than any previously calculated silane reduction system. Inclusion of a catalytic Br?nsted acid further reduced the activation barrier and led to the first silane-mediated reduction of acyclic phosphine oxides at room temperature.

Palladium-catalyzed C–P(III) bond formation reaction with acylphosphines as phosphorus source

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.

TRIPHENYLPHOSPHINE DERIVATIVES

The present invention relates to a triphenylphosphine of Formula (I) wherein M is a proton or a monovalent or divalent cation, n is an integer selected from 1 and 2, p takes a value selected from 1/2, 1 and 2, R1 is selected from H, C1-C18 alkyl, CF3 and SO3-, R11, R12 and R13 are independently selected from H and C1-C18 alkyl, with the proviso that if R1 is SO3-, then the product of n and p is equal to 2, R2, R3 and R5 are independently selected from H and C1-C18 alkyl, R4 is H, R6-R10 are independently selected from H, C1-C18 alkyl and CF3, at least one of R6-R10 being CF3; if R1 is not SO3-, then the product of n and p is equal to 1, R1-R10 are independently selected from H, C1-C18 is alkyl and CF3, at least one of the groups R1 -R10 being CF3; the present invention also is directed to a process for obtaining a triphenyl phosphine of Formula (I) and its use as ligand in the catalysis field and other several applications.

Homolytic substitution at phosphorus for the synthesis of alkyl and aryl phosphanes

(Chemical Equation Presented) A transition-metal-free radical phosphonation using Me3SnPPh2 and the less toxic Me 3SiPPh2 is reported. These readily available reagents react highly efficiently with primary and secondary alkyl radicals. Moreover, aryl radicals and tertiary alkyl radicals are phosphonated with Me 3SnPPh2 (see scheme; R = aryl, alkyl, vinyl; X = 1, Br, OC(S)imidazolyl). DFT calculations provide insights into the mechanism of the reaction.