5032-51-9

Upstream product

• 5032-55-3 (4-methoxycarbonylphenyl)diphenylphosphine oxide 
• 67-56-1 methanol 
• 2129-31-9 4-diphenylphosphanobenzoic acid 
• 17763-71-2 4-carbomethoxyphenyl triflate 
• 1257322-25-0 methyl 4-(diphenylphosphanyl)benzoate borane 
• 829-85-6 diphenylphosphane 
• 619-44-3 methyl 4-iodobenzoate 
• 40841-62-1 (diphenylphosphino)(p-tolyl)methanone 
• 1079-66-9 chloro-diphenylphosphine 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 4376-01-6 sodium diphenylphosphide 
• 1031-93-2 diphenyl(p-tolyl)phosphine 
• 603-35-0 triphenylphosphine 
• 7650-91-1 benzyldiphenylphosphane 

Downstream Products

• 2129-31-9 4-diphenylphosphanobenzoic acid 
• 1160705-20-3 4-diphenylphosphinylbenzenecarboxylic acid 4-[N-(3-trimethoxysilylpropyl)amide] 
• 1257322-25-0 methyl 4-(diphenylphosphanyl)benzoate borane 
• 625385-17-3 trans-[Rh(CO)Cl(4-Ph₂PC₆H₄COOCH₃)2] 

Relevant academic research and scientific papers

Studies on the interaction between poly-phosphane gold(I) complexes and dihydrofolate reductase: An interplay with nicotinamide adenine dinucleotide cofactor

A class of gold(I) phosphane complexes have been identified as inhibitors of dihydrofolate reductase (DHFR) from E. coli, an enzyme that catalyzes the reduction of dihydrofolate (DHF) to tetrahydrofolate (THF), using NADPH as a coenzyme. In this work, to

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.

A practical synthesis of unsymmetrical triarylphosphines by heterogeneous palladium(0)-catalyzed cross-coupling of aryl iodides with diphenylphosphine

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

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.

Organocatalyzed Reduction of Tertiary Phosphine Oxides

A novel selective catalytic reduction method of tertiary phosphine oxides to the corresponding phosphines has been developed. Notably, the reaction proceeds smoothly with low catalyst loadings of 1-5 mol% even at low temperature (70 C). Under the optimized conditions various phosphine oxides could be selectively reduced and the desired phosphines were usually obtained in excellent yields above 90%. Furthermore, we have developed a one-pot reaction sequence for the preparation of valuable phosphinborane adducts. Simple addition of BH3THF subsequent to the reduction step gave the desired adducts in yields up to 99%.

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.

A rhodium triphenylphosphine catalyst for alkene hydrogenation supported on neat superparamagnetic iron oxide nanoparticles

A phosphonic acid functionalized triphenylphosphine rhodium complex was synthesized and grafted onto neat superparamagnetic iron oxide nanoparticles. The material was investigated by elemental analysis, IR spectroscopy, thermogravimetric analysis, XRD, N2-physisorption analyses, and TEM measurements. The obtained hybrid material could be used as a catalyst for the hydrogenation of alkenes with excellent yields and a broad substrate scope. The catalyst can be reused ten times without any loss of activity. According to the results from X-ray absorption spectroscopy, it is likely that formation of Rh nanoparticles occurs during the reaction.

A recyclable ruthenium(ii) complex supported on magnetic nanoparticles: A regioselective catalyst for alkyne-azide cycloaddition

A magnetically separable ruthenium catalyst was synthesized through immobilizing a pentamethylcyclopentadienyl ruthenium complex on iron oxide nanoparticles. The catalyst is highly active and selective for the synthesis of 1,5-disubstituted 1,2,3-trizoles

Highly chemoselective metal-free reduction of phosphine oxides to phosphines

Unprecedented chemoselective reductions of phosphine oxides to phosphines proceed smoothly in the presence of catalytic amounts of specific Br?nsted acids. By utilizing inexpensive silanes, e.g., PMHS or (EtO)2MeSiH, other reducible functional groups such as ketones, aldehydes, olefins, nitriles, and esters are well-tolerated under optimized conditions.