53144-71-1

Upstream product

• 1015-38-9 diphenylphosphinodithioic acid 
• 104-81-4 4-Methylbenzyl bromide 
• 4559-70-0 Diphenylphosphine oxide 
• 159386-41-1 1-[Chloro-(diphenyl-phosphinoyl)-methyl]-4-methyl-benzene 
• 4020-99-9 diphenylphosphinous acid methyl ester 
• 185146-95-6 C₂₀H₁₉P 
• 104-87-0 4-methyl-benzaldehyde 
• 1079-66-9 chloro-diphenylphosphine 
• 589-18-4 4-Methylbenzyl alcohol 
• 2947-61-7 (4-methylphenyl)acetonitrile 
• 622-47-9 4-tolylacetic acid 
• 36838-04-7 α-Oxo-phenylmethan-diphenylphosphin 
• 829-85-6 diphenylphosphane 
• 98-88-4 benzoyl chloride 

Downstream Products

• 88618-84-2 Diphenyl-(4-brommethyl-benzyl)-phosphinoxid 
• 18869-29-9 (E)-4,4'-dimethylstilbene 
• 83248-27-5 1-bromo-1-(p-methylphenyl)-2,2-diphenylethene 
• 141172-18-1 1,2,3-trimethoxy-5-[(E)-2-(4-methylphenyl)ethenyl]benzene 
• 17555-94-1 (E)-4'-methoxy-4-methylstilbene 

Relevant academic research and scientific papers

Transition-Metal-Free and Base-Promoted Carbon-Heteroatom Bond Formation via C-N Cleavage of Benzyl Ammonium Salts

A facile and general method for constructing carbon-heteroatom (C-P, C-O, C-S, and C-N) bonds via C-N cleavage of benzyl ammonium salts under transition-metal-free conditions was reported. The combination of t-BuOK and 18-crown-6 enabled a wide range of substituted benzyl ammonium salts to couple readily with different kinds of heteroatom nucleophiles, i.e. hydrogen phosphoryl compounds, alcohols, thiols, and amines. Good functional group tolerance was demonstrated. The scale-up reaction and one-pot synthesis were also successfully performed.

Palladium-catalyzed phosphorylation of benzyl ammonium triflates with P(O)H compounds

A palladium-catalyzed phosphorylation of benzyl ammonium triflates with P(O)H compounds has been developed. Various benzylphosphorus compounds were produced in good to excellent yields with high functional group tolerance. All the three kinds of hydrogen phosphoryl compounds, i.e. H-phosphonates, H-phosphinates and secondary phosphine oxides, were applicable to this reaction. The successful scale-up experiment and one-pot synthetic operation also well demonstrated its practicality.

Copper-catalyzed C–P cross-coupling of arylmethyl quaternary ammonium salts via C–N bond cleavage

Abstract: A ligand-free copper-catalyzed C–P cross-coupling reaction of arylmethyl quaternary ammonium salts and diarylphosphine oxides in air is developed. Arylmethyl quaternary ammonium salts with various functional groups and a variety of dialkyl- and diarylphosphine oxides afford C–P cross-coupling products with good yields. This protocol requires no inert atmosphere, no ligand, and simple operation steps. Graphic abstract: [Figure not available: see fulltext.].

Palladium-catalyzed C(sp3)–P(III) bond formation reaction with acylphosphines as phosphorus source

Palladium-catalyzed C(sp3)–P(III) bond formation reaction for alkyl substituted phosphines preparation was developed. In this reaction, various alkyl bromides and limited alkyl chlorides reacted with acylphosphine under relative mild and easily accessible condition, and differential phosphines were afforded in good yields. This reaction made up the application of palladium catalysis in C(sp3)–P(III) bond formation, and indicated a practical application of acylphosphine as a phosphination reagent.

Controllable phosphorylation of thioesters: Selective synthesis of aryl and benzyl phosphoryl compounds

The controllable phosphorylations of thioesters were developed. When the reaction was catalyzed by a palladium catalyst, aryl or alkenyl phosphoryl compounds were generated through decarbonylative coupling, while the benzyl phosphoryl compounds were produced through deoxygenative coupling when the reaction was carried out in the presence of only a base.

Catalytic Deoxygenative Coupling of Aromatic Esters with Organophosphorus Compounds

We have developed a deoxygenative coupling of aromatic esters with diarylphosphine oxides/dialkyl phosphonates under palladium catalysis. In this reaction, aromatic esters can work as novel benzylation reagents to give the corresponding benzylic phosphorus compounds. The key of this reaction is the use of phenyl esters, an electron-rich diphosphine as a ligand, and sodium formate as a hydrogen source. Arylcarboxylic acids were also applicable in this reaction using (Boc)2O as an additive. Palladium/dcype worked to activate the acyl C-O bond of the ester and to support the reduction with sodium formate.

Preparation method of arylalkyl phosphorus oxide compounds

A preparation method of arylalkyl phosphorus oxide compounds is provided. The invention discloses a preparation method of several arylalkyl phosphorus oxide compounds. The preparation method includes:taking diphenylphosphine oxyhydrogen of 1.3 equivalent, 2.5% by mass nickel catalyst (with or without ligands) or palladium catalyst with ligands and a base of 1.5 equivalent from a glovebox, addingthem sequentially into a Schlenk reaction tube, adding a nitrile compound of 1.0 equivalent, vacuumizing, and backfilling with nitrogen; in the nitrogen atmosphere, adding a solvent, and allowing reaction to occur continuously at 120 DEG C for 16 h; after reaction, cooling to room temperature, and performing column chromatography separation to obtain the target product under high selectivity and high yield. The preparation method herein allows sp3C-CN\P-H cross coupling; reaction conditions are mild; operating is easy; the preparation process is simple; the target product has high conversion rate and high yield; the problems of other synthetic methods are solved that, for instance, two-step reaction system is complex, many organic and inorganic byproducts are produced, environmental pollution is caused easily, and the substrate range is narrow; the preparation method has a good industrial application prospect.

Preparation method of aryl methyl phosphine acylate

The invention discloses a preparation method of aryl methyl phosphine acylate. The method uses (hetero) aryl acetic acid as the starting material, and the raw materials are easily available and have agreat variety. The product obtained by the method provided by the invention has various types and wide uses. The aryl methyl phosphine acylate can be easily converted into a bis (hetero)arylethene derivative, and the compound can be used for preparation of dyes, fluorescent agents, whiteners, light-emitting diodes and other devices. In addition, the method disclosed by the invention has the advantages of easily available, stable and low toxicity raw materials, mild reaction conditions, high yield of target product, low pollution, simple reaction operation and post-treatment process, and is suitable for industrial production.

Synthetic method of diarylbenzylphosphine oxide compound

The invention provides a method for preparing a diarylbenzylphosphine oxide compound from a diarylphosphine oxide compound and a benzaldehyde derivative. The method has the following characteristics:raw materials are cheap and easily-available; a reaction

Catalytic sp3C-CN Bond Cleavage: Ni-Mediated Phosphorylation of Alkylnitriles

A direct phosphorylation of the sp3C-CN bond catalyzed by a nickel catalyst is disclosed. A wide range of primary nitriles readily coupled with secondary phosphine oxides to produce the corresponding phosphorylated products in high yields. As a key step, this new method was applied to the synthesis of anticancer drug Combretastatin-A4, significantly shortening its synthetic path.