15104-45-7

Upstream product

• 132993-23-8 4-fluorophenyl trifluoromethanesulfonate 
• 868-85-9 Dimethyl phosphite 
• 371-41-5 4-Fluorophenol 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 460-00-4 1-Bromo-4-fluorobenzene 
• 732306-64-8 bis(4-fluorophenyl)iodonium triflate 
• 121-45-9 phosphorous acid trimethyl ester 
• 352-34-1 4-fluoro-1-iodobenzene 
• 371-14-2 4-fluorophenylhydrazine 

Downstream Products

• 18437-74-6 1-(dimethyl-phosphinoyl)-4-fluoro-benzene 

Relevant academic research and scientific papers

Photoinduced Transition-Metal-Free Cross-Coupling of Aryl Halides with H-Phosphonates

Photoinduced transition-metal- and photosensitizer-free cross-coupling of aryl halides (including Ar-Cl, Ar-Br, and Ar-I) with H-phosphonates (including dialkyl phosphonates and diarylphosphine oxides) is reported. Various functional groups were tolerated, including ester, methoxy, dimethoxy, alkyl, phenyl, trifluoromethyl, and heterocyclic compounds. This simple and green strategy provides a practical pathway to synthesize arylphosphine oxides.

C-P bond formation of cyclophanyl-, and aryl halides: Via a UV-induced photo Arbuzov reaction: A versatile portal to phosphonate-grafted scaffolds

A new versatile method for the C-P bond formation of (hetero)aryl halides with trimethyl phosphite via a UV-induced photo-Arbuzov reaction, accessing diverse phosphonate-grafted arenes, heteroarenes and co-facially stacked cyclophanes under mild reaction

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.

A mild electroassisted synthesis of (hetero)arylphosphonates

The electrochemically-assisted synthesis of (hetero)arylphosphonates from (hetero)aryl halides and dimethyl phosphite is described. Very mild and simple conditions are employed as the cross-coupling is carried out in galvanostatic mode, in an undivided ce

A dual catalytic strategy for carbon-phosphorus cross-coupling via gold and photoredox catalysis

A new method for the P-arylation of aryldiazonium salts with H-phosphonates via dual gold and photoredox catalysis is described. The reaction proceeds smoothly at room temperature in the absence of base and/or additives, and offers an efficient approach t

Copper-catalyzed coupling reaction of arylhydrazines and trialkylphosphites

A novel CuO-catalyzed coupling reaction of arylhydrazines with trialkyl phosphites to afford arylphosphonates is described. The reaction proceeded at 80 C in air without external reductants, oxidants, and ligands.

Direct conversion of phosphonates to phosphine oxides: An improved synthetic route to phosphines including the first synthesis of methyl JohnPhos

The synthesis of tertiary phosphine oxides from phosphonates was achieved reliably and in good to excellent yields using stoichiometric amounts of alkyl or aryl Grignard reagents and sodium trifluoromethanesulfonate (NaOTf). In the absence of the NaOTf additive, covalent coordination oligomers of magnesium and phosphorus species dominate the reaction, producing very low yields of phosphine oxide, but high conversions of the phosphonate starting material. Mechanistic studies revealed that a five-coordinate phosphorus species - not a phosphinate - is the reaction intermediate. A diverse array of phosphonates was converted to phosphine oxides using a variety of Grignard reagents for direct carbon-phosphorus functionalization. This new methodology especially simplifies the synthesis of dimethylphosphino (RPMe2)-type phosphines by using air-, water-, and silica-stable intermediates. To highlight this reaction, a new Buchwald-type ligand ([1,1′-biphenyl]-2-yldimethylphosphine, or methyl JohnPhos) and a classic bidentate phosphine, bis(diphenylphosphino)propane (dppp), were synthesized in excellent yields.