13175-77-4

Upstream product

• 88652-74-8 (2-bromophenyl)diphenylphosphine oxide 
• 16419-60-6 2-Methylphenylboronic acid 
• 13379-29-8 2-bromo-2'-(bromomethyl)-1,1'-biphenyl 
• 251320-87-3 2-bromo-2'-methylbiphenyl 
• 402822-72-4 1-diphenylphosphino-2'-methylbiphenyl 
• 13175-75-2 2'-diphenylphosphino-2-methoxymethylbiphenyl 
• 13175-92-3 9,10-dihydro-9,9-diphenyl-9-phosphoniaphenanthrene bromide 
• 69200-16-4 2'-bromo-[1,1'-biphenyl]-2-carboxylic acid 
• 13175-74-1 2'-bromo-2-methoxymethylbiphenyl 
• 13175-73-0 (2'-bromo-biphenyl-2-yl)-methanol 
• 62336-24-7 (2-bromophenyl)diphenylphosphane 
• 829-85-6 diphenylphosphane 
• 4559-70-0 Diphenylphosphine oxide 
• 583-55-1 1-Bromo-2-iodobenzene 

Downstream Products

• 402822-72-4 1-diphenylphosphino-2'-methylbiphenyl 
• 1601392-64-6 C₂₇H₂₃O₃P 

Relevant academic research and scientific papers

A highly efficient catalyst for Suzuki coupling of aryl halides and bromoarylphosphine oxides

The biphenyl-based phosphine, P(o-C6H4C6H4Me)Ph2, is a moderately bulky and electron-rich phosphine, which has been successfully applied to the palladium catalyzed Suzuki coupling of activated and deactivated aryl halides as well as bromoarylphosphines and bromoarylphosphine oxides, with low catalyst loading and good to excellent conversions and turnovers.

Ruthenium-Catalyzed Gram-Scale Preferential C-H Arylation of Tertiary Phosphine

A general protocol for site-preferential mono-C-H arylation of tertiary phosphine ligands catalyzed by a ruthenium(II) complex was devised. This protocol gives access to a series of modified Buchwald-biaryl monophosphines on a gram scale in moderate to excellent yields. A catalytic cycle is proposed derived from knowledge of the intermediates observed by ESI-MS. Importantly, these monoarylated products could be further transformed into dibenzophosphole derivatives.

Palladium-catalyzed R2(O)P directed C(sp2)-H acetoxylation

A novel and efficient Pd-catalyzed C-H acetoxylation is described. The approach uses R2(O)P as a directing group to synthesize various substituted 2′-phosphorylbiphenyl-2-OAc compounds. Notably, the reaction exhibits smooth operation under mild conditions and shows good functional group tolerance. Products are obtained with high selectivity and yields. This journal is the Partner Organisations 2014.

Palladium-catalyzed P(O)R2 directed C-H arylation to synthesize electron-rich polyaromatic monophosphorus ligands

Palladium-catalyzed arylation of (diisopropylphosphoryl)biphenyl skeleton derivatives by the P(O)R2 directed C-H functionalization was reported. The related products were obtained in high regioselectivity and good functional group tolerance was observed. This reaction provided a new and efficient pathway for the synthesis of polyaromatic monophosphorus ligands. The Royal Society of Chemistry.

Pd(II)-catalyzed C(sp2)-H hydroxylation with R 2(O)P-coordinating group

A novel R2(O)P-directed Pd(II)-catalyzed C-H hydroxylation to synthesize various substituted 2′-phosphorylbiphenyl-2-ol compounds is described. Notably, the reaction operates under mild conditions and shows good functional group tolerance, high selectivity, and yield.

Synthesis and applications of a new palladacycle as a high active catalyst in the Suzuki couplings

The reaction of biphenyl-based phosphine P(o-C6H4Me)Ph2 (1) with Pd(OAc)2 in toluene affords the air and water stable palladacycle (2) as a binuclear compound which has been characterized by multi-nuclear NMR spectroscopy and elemental analysis as a mixture of cis and trans isomers with relative intensity of 1:3, respectively. This palladacycle is a highly efficient catalyst precursor for the coupling of aryl boronic acids and aryl halides. Both activated and deactivated aryl bromides and chlorides are efficiently coupled in the presence of 2 to furnish the corresponding cross-coupled products in excellent yields, and a wide variety of functional groups are tolerated in aryl halides. This methodology has also been extended for the coupling of bromoarylphosphines and bromoarylphosphine oxides with aryl boronic acids for the generation of hindered corresponding products.

Palladium-catalysed synthesis of biaryl phosphines

Monodentate, biphenyl-type phosphines have emerged as a powerful class of ligands in homogeneous catalysis. Synthetic methods for these ligands are limited, however. We report that the palladium-catalysed Suzuki coupling of OPR2(o-C6H4X) (R=Ph, t-Bu; X=Br, I) with arylboronic acids affords a variety of biaryl phosphine oxides including those that contain heterocycles. The corresponding phosphines are readily obtained by treatment with HSiCl3. The methodology provides an easy entry to monodentate biaryl and heterobiaryl Poverlapping logical AND signX (X=N, O, S) phosphines with diverse steric and electronic properties.

Synthesis of biphenyl-based phosphines by Suzuki coupling

A series of phosphine oxides has been synthesised by the palladium-catalysed Suzuki coupling of arylboronic acids with OPPh2(o-C6H4Br). On reduction with trichlorosilane, functionalised, biphenyl-based phosphine ligands were obtained in good yields. Our preliminary results indicate these ligands to be effective for palladium-catalysed C-C coupling reactions including the formation of their own oxides.