2373-43-5

Usage

Synthesis Reference(s)

Synthesis, p. 56, 1981 DOI: 10.1055/s-1981-29335

InChI:InChI=1/C10H14ClO3P/c1-3-13-15(12,14-4-2)10-7-5-9(11)6-8-10/h5-8H,3-4H2,1-2H3

Upstream product

• 108-90-7 chlorobenzene 
• 762-04-9 phosphonic acid diethyl ester 
• 106-39-8 bromochlorobenzene 
• 122-52-1 triethyl phosphite 
• 637-87-6 1-Chloro-4-iodobenzene 
• 7446-70-0 aluminium trichloride 
• 7719-12-2 phosphorus trichloride 
• 1005-33-0 4-chlorophenyldichlorophosphine 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 14752-66-0 sodium p-chlorobenzenesulphinate 
• 21700-74-3 (p-chlorophenyl)triethoxysilane 
• 122-01-0 4-chloro-benzoyl chloride 
• 195062-61-4 4-chlorophenylboronic acid pinacol ester 
• 1073-69-4 N-4-chlorophenylhydrazine 

Downstream Products

• 5431-35-6 4-chlorophenylphosphonic acid 
• 128333-52-8 (4-Chloro-phenyl)-phosphonic acid monohexyl ester 
• 1605306-33-9 C₁₁H₁₃ClNO₃P 

Relevant academic research and scientific papers

Fe-MIL-101 modified by isatin-Schiff-base-Co: a heterogeneous catalyst for C-C, C-O, C-N, and C-P cross coupling reactions

A metal-organic framework functionalized with a cobalt-complex is preparedviapost-synthetic modification of Fe-MIL-101-NH2. Initially, Fe-MIL-101-NH2reacted with isatin to produce Fe-MIL-101-isatin-Schiff-base, which can anchor the cobalt by the addition of cobalt acetate. The resulting MOF-Co catalyst is characterized by employing multiple techniques. This new modified MOF acts as a heterogeneous and recyclable catalyst for efficient Ullmann, Buchwald-Hartwig, Hirao, Hiyama and Mizoroki-Heck cross-coupling reactions of several aryl halides/phenylboronic acid/phenyltosylate with phenols, anilines/heterocyclic amines, triethyl phosphite, triethoxyphenylsilane and alkenes and generates the expected coupling products in good to high yields.

Palladium-catalyzed one-pot phosphorylation of phenols mediated by sulfuryl fluoride

We report a general palladium-catalyzed one-pot procedure for the synthesis of phosphonates, phosphinates and phosphine oxides from phenols mediated by sulfuryl fluoride. It features mild conditions, broad substrate scope, high functionality tolerance and water insensitivity. The utility of this procedure has been well demonstrated by gram-scale synthesis, sequential synthesis of click chemistry building blocks, late-stage decoration of drugs and natural products and on-DNA synthesis of phosphine oxide for a DNA-encoded library (DEL).

A hydrophilic heterogeneous cobalt catalyst for fluoride-free Hiyama, Suzuki, Heck and Hirao cross-coupling reactions in water

A hydrophilic heterogeneous cobalt catalyst of chitosan, denoted as mTEG-CS-Co-Schiff-base, has been successfully prepared. This newly synthesized catalyst was characterized by different methods such as XRD, FE-SEM, TEM, TGA, FT-IR, 13C{1H} CP/MAS NMR, XPS and ICP analyses. The catalyst displayed excellent activity for the palladium and fluoride-free Hiyama, Suzuki, Heck and Hirao reactions of various aryl iodides, bromides and chlorides (i.e., the most challenging aryl halides which are cheaper and more widely available than aryl iodides and bromides) in water. The presence of triethylene glycol tags with hydrophilic character on the Co-complex supported on chitosan provides dispersion of the catalyst particles in water, which leads to higher catalytic performance and also facile catalyst recovery by successive extraction. It was reused for at least six successive runs without any discernible decrease in its catalytic activity or any remarkable changes in catalyst structure. The use of water as a green solvent, without requiring any additive or organic solvent, as well as use of a low cost and abundant cobalt catalyst instead of expensive Pd catalysts along with the catalyst recovery and scalability, make this method favorable from environmental and economic points of view for the C-C and C(sp2)-P coupling reactions. Notably, this is the first report on the application of a cobalt catalyst in Hiyama reactions.

C-P bond construction catalyzed by NiII immobilized on aminated Fe3O4@TiO2 yolk-shell NPs functionalized by (3-glycidyloxypropyl)trimethoxysilane (Fe3O4@TiO2 YS-GLYMO-UNNiII

NiII immobilized on aminated Fe3O4@TiO2 yolk-shell NPs functionalized by (3-glycidyloxypropyl)trimethoxysilane (Fe3O4@TiO2 YS-GLYMO-UNNiII) was prepared as a stable, h

Catalyst-free phosphorylation of aryl halides with trialkyl phosphites through electrochemical reduction

A catalyst-free electrochemical cross-coupling reaction of aryl halides with trialkyl phosphite has been developed. This reaction proceeds in an undivided cell with a low-cost Ni anode and a graphite cathode under mild and neutral conditions. A wide range of functional groups are well-tolerated and the phosphorylated product can be obtained on the gram scale, showing that this transformation has the potential to be a valuable method for the construction of aromatic carbon-phosphorus bonds.

Nickel-Catalyzed Electrochemical Phosphorylation of Aryl Bromides

A nickel-catalyzed electrochemical cross-coupling reaction of aryl bromides with dialkyl phosphites, ethyl phenylphosphinate, and diphenylphosphine oxide has been developed. This reaction utilizes a simple undivided cell with inexpensive carbon electrodes to synthesize aryl phosphonates, aryl phosphinates, and arylphosphine oxides at room temperature. This protocol provides a mild and efficient route for the construction of C-P bond in moderate to high yields with broad substrate scope.

Decarbonylative Phosphorylation of Carboxylic Acids via Redox-Neutral Palladium Catalysis

We describe the direct synthesis of organophosphorus compounds from ubiquitous aryl and vinyl carboxylic acids via decarbonylative palladium catalysis. The catalytic system shows excellent scope and tolerates a wide range of functional groups (>50 examples). The utility of this powerful methodology is highlighted in the late-stage derivatization directly exploiting the presence of the prevalent carboxylic acid functional group. DFT studies provided insight into the origin of high bond activation selectivity and P(O)-H isomerization pathway.

Arylphosphate compound and preparation method thereof

The invention discloses an arylphosphate compound and a preparation method thereof. The preparation method includes, with arylamine and phosphite ester as reactants and tert-butyl nitrite as an accelerator, performing stirring reaction at the temperature within 70-80 DEG C for 40-60 minutes, and separating through the column chromatography to obtain a product, namely arylphosphate compound. The preparation method is a new way of synthetizing arylphosphate target compound from low-price feasible raw materials of arylamine and phosphite ester on the acid-free and metal-free condition, has the advantages of mild reaction condition, operational simplicity and the like and overcomes the big trouble to production of medical intermediates caused by residues of metal catalysts, after-treatment ofacids in medicine synthesis, and accordingly, the simple and efficient meta-free and acid-free catalysis system has great potential application value and economic benefit.

Visible-Light-Mediated Metal-Free Synthesis of Aryl Phosphonates: Synthetic and Mechanistic Investigations

This work describes a straightforward access to a large variety of aryl phosphonates by the simple combination of diaryliodonium salts with phosphites in the presence of a base and under visible-light illumination. The reaction proceeds smoothly, tolerates various functionalities, and was applied for the synthesis of pharmaceutically relevant compounds. Mechanistic investigations, including EPR, NMR, and DFT calculations, support the postulated reaction mechanism.

Aryl phosphate esters compound and preparation method thereof

The invention discloses an aryl phosphate esters compound and a preparation method thereof, wherein an organic dye is used as a photosensitizer, a catalytic amount of alkali is added, aryl hydrazine and phosphate are used as reactants, acetonitrile is used as a solvent, the temperature is controlled between 25-45 DEG C, the reaction is carried out under the irradiation of visible light for 1-6h, and the product aryl phosphate compound is separated by column chromatography. The invention provides a new method for synthesizing aryl phosphate class target compound with cheap and easily availablearyl hydrazine and phosphate ester compound as starting material for the first time. The preparation method has the advantages of mild reaction conditions, simple operation and the like; in the drug synthesis, the residual of the metal catalyst brings great trouble to the production and application of the drug, so that the metal-free catalytic system in the method has great potential application value.