35144-01-5

Usage

Uses

Used in Organic Synthesis:
(R)-(2-Methoxyphenyl)methylphenylphosphine is used as a reagent in organic synthesis for its ability to participate in various chemical reactions due to the presence of the phosphorus atom, which can form coordination complexes.
Used in Transition Metal Chemistry:
In the field of transition metal chemistry, (R)-(2-Methoxyphenyl)methylphenylphosphine is used as a ligand, playing a crucial role in catalytic processes. Its unique structure allows for the formation of stable complexes with transition metals, enhancing the efficiency and selectivity of the reactions.
Used in Metal-Catalyzed Reactions:
(R)-(2-Methoxyphenyl)methylphenylphosphine is also utilized in metal-catalyzed reactions, where it can improve the performance of catalysts by stabilizing intermediates and facilitating the reaction pathways.
Used in Pharmaceutical Industry:
(R)-(2-Methoxyphenyl)methylphenylphosphine may find applications in the pharmaceutical industry, where its unique reactivity and coordination properties can be harnessed for the development of new drugs and drug delivery systems.
Used in Material Science:
In material science, (R)-(2-Methoxyphenyl)methylphenylphosphine could be employed in the synthesis of novel materials with specific properties, such as improved conductivity or catalytic activity, by leveraging its ability to form coordination complexes with various metals.
Overall, (R)-(2-Methoxyphenyl)methylphenylphosphine is a valuable compound in the fields of organic and inorganic chemistry, with potential applications in various industries, including pharmaceuticals and material science, due to its unique structure and reactivity.

Upstream product

• 5761-97-7 methyl(phenyl)phosphinic chloride 
• 16750-63-3 2-methoxyphenylmagnesium bromide 
• 129212-59-5 (R(P))-(o-anisyl)(methyl)(phenyl)phosphine-P-borane 
• 87214-08-2 C₁₇H₂₁INOP 
• 87248-41-7 (2S,4R,5S)-3,4-Dimethyl-2,5-diphenyl-[1,3,2]oxazaphospholidine 
• 1636-14-2 bis(diethylamino)phenylphosphine 
• 6389-79-3 (+)-(R)_p methyl methylphenylphosphinate 
• 94669-51-9 C₃₃H₃₅N₂O₂P 
• 94669-51-9 C₃₃H₃₅N₂O₂P 
• 94669-47-3 C₂₅H₂₆ClN₂OP 
• 644-97-3 Dichlorophenylphosphine 
• 152846-35-0 (S)-(-)-(o-anisyl)methylphenylphosphine sulfide 
• 35143-99-8 (R_p)-(2-methoxyphenyl)methylphenylphosphine oxide 
• 20663-35-8 (S_p)-(2-methoxyphenyl)methylphenylphosphine oxide 

Downstream Products

• 35143-99-8 (R_p)-(2-methoxyphenyl)methylphenylphosphine oxide 
• 20663-35-8 (S_p)-(2-methoxyphenyl)methylphenylphosphine oxide 
• 1401061-63-9 C₃₀H₃₈O₂P⁽¹⁺⁾*Cl^(1-) 
• 1401061-64-0 C₃₀H₃₈O₂P⁽¹⁺⁾*Cl^(1-) 
• 129212-59-5 (R(P))-(o-anisyl)(methyl)(phenyl)phosphine-P-borane 
• 1485-88-7 (o-methoxyphenyl)methylphenylphosphine 
• 20663-35-8 (2-methoxyphenyl)(methyl)(phenyl)phosphine oxide 
• 1486-34-6 Dimethyl-<2'-methoxy-phenyl>-phenyl-phosphonium-2,4-dinitrobenzol-sulfonat 
• 97764-41-5 (S)-(+)-(o-anisyl)(methyl)phenylphosphine/borane complex 
• 176697-32-8 (1-tBu-3,4-Me2C5H2)(C5H5)Ta(μ-CO)(μ-PMe2)W(CO)5(PMePh(o-C6H4OMe)) 
• 68811-61-0 bicyclo[2.2.1]heptadiene bis((R)-o-methoxyphenylmethylphenylphosphino)rhodium(I) tetrafluoroborate 
• 133396-22-2 (η4-1.5-cyclooctadiene)bis{(S)-(2-methoxyphenyl)(methyl)(phenyl)phosphine}iridium(I) 

Relevant academic research and scientific papers

Reduction of tertiary phosphine oxides to phosphine-boranes using Ti(Oi-Pr)4/BH3-THF

A new method for reduction of tertiary phosphine oxides leading to the formation of tertiary phosphine-boranes has been developed. The BH3-THF/Ti(Oi-Pr)4 reducing system enables conversion of triaryl, diarylalkyl and trialkylphosphine oxides directly to their borane analogues in good to high yields. In contrast to the previously reported protocols, the presence of activating groups in the structure of starting material is not necessary for the reaction to occur. The reaction is highly stereoselective and proceeds with predominant retention of configuration at the phosphorus atom. A plausible mechanism of reduction of the P[dbnd]O bond by BH3-THF/Ti(Oi-Pr)4 has been proposed.

Formation of unexpected heterocyclic products from pyrolysis of thiocarbonyl stabilised phosphonium ylides

Chiral phthalimido thioxo-stabilised phosphonium ylides, prepared starting from (S)-alanine and (S)-phenylalanine, undergo intramolecular Wittig reaction upon pyrolysis leading to the previously unknown pyrrolo[2,1-a]isoindol-5-one-2- thiones, rather than

Catalyzing pyramidal inversion: Configurational lability of P-stereogenic phosphines via single electron oxidation

We report that pyramidal inversion of trivalent phosphines may be catalyzed by single electron oxidation. Specifically, a series of P-stereogenic (aryl)methylphenyl phosphines are shown to undergo rapid racemization at ambient temperature when exposed to catalytic quantities of a single electron oxidant in solution. Under these conditions, transient phosphoniumyl radical cations (R3P?+) are formed, and computational models indicate that the pyramidal inversion barriers for these open-shell intermediates are on the order of ～5 kcal/mol. The observed 1020-fold rate enhancement over uncatalyzed pyramidal inversion opens new opportunities for the dynamic stereochemistry of phosphines and may hold additional implications for the configurational stability of P-stereogenic phosphine ligands on high-valent oxidizing transition metals.

Identification of a key intermediate in the asymmetric Appel process: One pot stereoselective synthesis of P-stereogenic phosphines and phosphine boranes from racemic phosphine oxides

Sequential treatment of racemic phosphine oxides with oxalyl chloride and chiral non-racemic alcohol generates the same ratios of diastereomeric alkoxyphosphonium salts obtained in the corresponding asymmetric Appel process, strongly implicating the intermediate chlorophosphonium salt in the stereoselecting step. Subsequent reduction allows a novel synthesis of enantioenriched P-stereogenic phosphines-phosphine boranes. The Royal Society of Chemistry 2012.

PROCESSES FOR THE STEREOSELECTIVE PREPARATION OF P-CHIRAL FOUR -COORDINATED PHOSPHORUS BORANE COMPOUNDS AND P-CHIRAL THREE-COORDINATED PHOSPHORUS COMPOUNDS

Processes for the stereoselective preparation of P-chiral four-coordinated phosphorus borane compounds and P-chiral three-coordinated phosphorus compounds.

A convenient and mild chromatography-free method for the purification of the products of Wittig and Appel reactions

A mild method for the facile removal of phosphine oxide from the crude products of Wittig and Appel reactions is described. Work-up with oxalyl chloride to generate insoluble chlorophosphonium salt (CPS) yields phosphorus-free products for a wide variety of these reactions. The CPS product can be further converted into phosphine.

Enantiodivergent synthesis of P-chirogenic phosphines

Several approaches for the enantiodivergent synthesis of P-chirogenic mono- and diphosphines are described, using ephedrine methodology and phosphine borane chemistry. Firstly, both enantiomers of a tertiary phosphine can be obtained starting from the same oxazaphospholidine borane complex, prepared from (+)-ephedrine, when changing the order of addition of the organolithium reagents during the synthetic pathway. The second approach is based on the chlorophosphine boranes, which react with an organolithium reagent, to afford the corresponding phosphines with inversion of configuration. In the case where the chlorophosphine borane reacts with the t-butyl lithium reagent, a metal-halogen exchange occurs to afford the corresponding phosphide borane with retention of the configuration. The reaction of the phosphide borane with an alkyl halide leads to the same phosphine, but with the opposite configuration. Another approach depends on the diastereoselective preparation of the starting oxazaphospholidine borane complex from (-)-ephedrine, which leads according the case, to either one or the other enantiomer of a phosphine. Finally, the synthesis of (R,R)- and (S,S)-1,2-bis(methylphenylphosphino)ethane is also demonstrated using both enantiomers of the P-chirogenic diphosphinite diborane, which simultaneously allows the introduction of alkyl- or aryl substituents on the phosphorus atoms. In summary, these approaches show the great efficiency of the "ephedrine methodology" for the enantiodivergent synthesis of P-chirogenic mono- and diphosphines, and bearing alkyl or aryl substituents.

Synthesis of P-stereogenic phosphorus compounds. Asymmetric oxidation of phosphines under appel conditions

Racemic phosphines are converted into enantioenriched phosphine oxides via a synthetically simple, but theoretically interesting, oxidation procedure in good enantiomeric excess (up to 80%) and excellent yields (>95%). These phosphine oxides can be oxidatively coupled to provide easy access to enantiopure DiPAMPO analogues. Particularly attractive aspects of this procedure are the operational simplicity and the low cost required to synthesize these high value compounds. Copyright

Stereospecific deoxygenation of phosphine oxides with retention of configuration using triphenylphosphine or triethyl phosphite as an oxygen acceptor

(Chemical Equation Presented) A new protocol for deoxygenation of various phosphine oxides with retention of configuration is described. The advantage of the new method includes milder conditions and considerably shortened reaction times. Mechanistic studies about the oxygen transfer between the starting phosphine oxide and the sacrificial triphenylphosphine are also presented.

Radical-based reduction of phosphine sulfides and phosphine selenides by (Me3Si)3SiH

Tris(trimethylsilyl)silane reacts with phosphine sulfides and phosphine selenides under free radical conditions to give the corresponding phosphines in good yields. Stereochemical studies on P-chiral phosphine sulfides show these reductions proceed with retention of configuration. (C) 2000 Elsevier Science Ltd.