402822-72-4

Usage

Uses

suzuki reaction

Upstream product

• 251320-87-3 2-bromo-2'-methylbiphenyl 
• 1079-66-9 chloro-diphenylphosphine 
• 16419-60-6 2-Methylphenylboronic acid 
• 829-85-6 diphenylphosphane 
• 62336-24-7 (2-bromophenyl)diphenylphosphane 
• 4559-70-0 Diphenylphosphine oxide 
• 88652-74-8 (2-bromophenyl)diphenylphosphine oxide 
• 583-55-1 1-Bromo-2-iodobenzene 
• 13175-77-4 (2'-methyl-[1,1'-biphenyl]-2-yl)diphenylphosphine oxide 

Downstream Products

• 13175-77-4 (2'-methyl-[1,1'-biphenyl]-2-yl)diphenylphosphine oxide 
• 1351394-96-1 (3^,-methyl-[1,1^,;2^,,1^,,]terphenyl-2^,,-yl)diphenylphosphine 
• 1601392-64-6 C₂₇H₂₃O₃P 
• 1342879-09-7 1-methyl-5-phenyl-5H-dibenzophosphole 

Relevant academic research and scientific papers

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.

Palladium-catalyzed direct synthesis of phosphole derivatives from triarylphosphines through cleavage of carbon-hydrogen and carbon-phosphorus bonds

(Phosp)hole in one: A palladium-catalyzed synthesis for directly assembling phosphole skeletons from triarylphosphines through C-H and C-P bond cleavage was developed. This approach overcomes several of the limitations of the so far reported methods. Phospholes bearing a range of functionalities (including Br, F, CO2Me, Ac, and CN) and an array of fused rings (naphthalenes, anthracenes, furans, and pyrroles) can be easily synthesized. Copyright

Selective arylation of 1,1-disubstituted olefins using a biphenyl-based phosphine in Heck coupling reactions

The biphenyl-based phosphine, 2-diphenylphosphino-2′-methylbiphenyl is an effective ligand for palladium-catalyzed terminal arylation of 1,1-disubstituted olefins with aryl bromides in DMF and K2CO3 as base. The yields of products are independent of the electronic properties of the aryl bromides, however, the nature of the olefin has a major effect.

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.

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.

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.

Water soluble phosphines Part XV. Syntheses of multiply functionalized and chiral phospine ligands by Pd-catalyzed P-C and C-C coupling reactions

Phosphine ligands containing mono- and multiply substituted aromatic substituents (1-13, 19a and 19b) are accessible in high yields by palladium-catalyzed P-C coupling reactions between primary, secondary or disecondary phosphines and iodo- or bromoaromatic compounds. The reaction is of broad applicability and compatible with electron donor or electron acceptor substituents in ortho, meta or para position to the halogen in the aromatic ring systems. It may be performed in protic and aprotic solvents. The chiral spirocyclic boronato complex 15a is formed upon reaction of 3 with boric acid, while with benzeneboronic acid 15c with a peripheral Lewis acid group is obtained. The Pd-mediated P-C coupling reaction of primary phosphines proceeds stepwise, tailor-made chiral secondary (16) and tertiary phosphines (17) being formed in high yield. Through combination with Suzuki-type C-C coupling reactions, the scope of Pd-catalyzed P-C coupling may be extended further, novel ligands (20a, 20b, 21a, 21b) with biphenylyl substituents being accessible. The X-ray structures of the salicylic acid derivative 3 (space group P1) and of ortho-iso-propylphenyl-diphenylphosphine 6 (space group Pbca) have been determined.

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.