4141-48-4

Usage

Uses

Used in Chemical Synthesis:
ALLYLDIPHENYLPHOSPHINE OXIDE is used as a reactant for the preparation of a-substituted alkylsilanes via regioand chemoselective copper-catalyzed silylzincation and electrophilic substitution from terminal alkenes. This application takes advantage of its reactivity with alkenes and silylzinc reagents to form the desired products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, ALLYLDIPHENYLPHOSPHINE OXIDE is used as a reactant for the preparation of α-substituted alcohols via Fleming-Tamao oxidation of alkylsilanes. This process is crucial for the synthesis of various pharmaceutical compounds, as α-substituted alcohols are important building blocks in drug development.
Used in Catalyst Preparation:
ALLYLDIPHENYLPHOSPHINE OXIDE is used in the olefin isomerization process with Grubbs' catalysts occluded in a hydrophobic matrix of polydimethylsiloxane (PDMS). Its interaction with the catalyst enhances the isomerization efficiency and selectivity, making it a valuable component in this application.
Used in Organic Chemistry:
In organic chemistry, ALLYLDIPHENYLPHOSPHINE OXIDE is used for the synthesis of C9-substituted trans-hydrindene via diastereotopic group-selective intramolecular Diels-Alder reaction. This reaction showcases the compound's ability to participate in complex organic transformations, leading to the formation of valuable synthetic intermediates.
Used in Catalyst Modification:
ALLYLDIPHENYLPHOSPHINE OXIDE is used in the isomerization of allyl group-containing compounds to propenyl group-containing compounds in the presence of a Grubbs second-generation Ru catalyst. This application highlights its role in modifying the catalyst's properties, enabling the selective transformation of allyl groups to propenyl groups.
Used in Material Science:
In material science, ALLYLDIPHENYLPHOSPHINE OXIDE is used in the ruthenium-catalyzed olefin cross-metathesis of vinyl and allyl phosphine oxides to give alkenyl phosphine oxides and bis-phosphine oxides. This process is essential for the development of new materials with specific properties, such as improved stability or reactivity.

InChI:InChI=1/C15H15OP/c1-2-13-17(16,14-9-5-3-6-10-14)15-11-7-4-8-12-15/h2-12H,1,13H2

Upstream product

• 14655-53-9 allyloxy-diphenylphosphane 
• 1498-47-1 allylphosphonic dichloride 
• 106-95-6 allyl bromide 
• 4559-70-0 Diphenylphosphine oxide 
• 762-73-2 trimethyl(allyl)stannane 
• 1499-21-4 Diphenylphosphinic chloride 
• 4569-35-1 (Z)-diphenyl 1,2-propenylphosphine oxide 
• 625-38-7 but-3-enoic acid 
• 603-35-0 triphenylphosphine 
• 791-28-6 Triphenylphosphine oxide 
• 15784-26-6 allyl t-butyl carbonate 
• 2129-89-7 diphenyl(methyl)phosphine oxide 
• 1079-66-9 chloro-diphenylphosphine 
• 719-80-2 Ethyl diphenylphosphinite 

Downstream Products

• 59971-02-7 Allyl-bis-(m-nitrophenyl)-phosphinoxid 
• 4252-89-5 diphenyl(prop-1-en-1-yl)phosphine oxide 
• 54664-11-8 2-(N-Diethylamino)propyldiphenylphosphinoxid 
• 113131-98-9 (E)-1-(diphenylaminophosphinyl)-3-trimethylsilylpropene 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 31915-94-3 (Z)-1-Phenylbuta-1,3-diene 
• 85048-22-2 (±)-1-(tert-butyl)-4-(2-propenylidene)cyclohexane 
• 114893-45-7 3-diphenylphosphinoyl-2-methylpent-4-en-2-ol 
• 136679-71-5 5-diphenylphosphinoylmethyl-3-phenyl-4,5-dihydroisoxazole 
• 25203-84-3 (Z)-buta-1,3-dien-1-ylcyclohexane 
• 25203-83-2 (E)-1-cyclohexyl-1,3-butadiene 
• 107326-64-7 (2E,7E)-1-(Benzyloxy)-2,7,9-decatriene 
• 107326-72-7 (2E,7E)-1-(Benzyloxy)-4-methyl-2,7,9-decatriene 
• 159428-64-5 (2E,7E)-1-(Benzyloxy)-5-(2-phenylethyl)-2,7,9-decatriene 

Relevant academic research and scientific papers

Use of tin derivatives for selective allylation and methylation of halogenophosphorus compounds

Palladium(0) catalyzed gem-dimethylation of hexachlorocyclotriphosphazene with tetramethylstannane is described as well as the high yield monoallylation of halogenophosphorus or -boron compounds by allyltrialkylstannanes under photolytic conditions.

Microwave heating in synthesis: Preparation of allyldiphenylphosphine oxide

A new one-pot synthesis of allyldiphenylphosphine oxide has been developed using a tandem Sn2'/Michaelis-Arbuzov sequence. The application of microwave heating lowers the reaction time significantly.

Synthesis, Structure, and Solution Studies of Lithiated Allylic Phosphines and Phosphine Oxides

This study reports a new series of 12 α-lithiated allylic phosphines and phosphine oxides. By incorporating Lewis base donors including diethyl ether (Et2O), tetrahydrofuran (THF), N,N,N′,N′,-tetramethylethylenediamine (TMEDA), and N,N,N′,N′,N″,-pentamethyldiethylenetriamine (PMDETA), nine complexes were structurally characterized by single-crystal X-ray crystallography. This includes novel dilithiated allylic phosphine 4 [PhP{CHCHCH2Li(TMEDA)}2] and a rare hemisolvated lithiated phosphine oxide 6 [{Ph2P(O)CHC(Me)CH2Li}2(TMEDA)]. Interestingly, in the solid state, P(III) complexes take advantage of Li-πinteractions to the newly formed delocalized system, in comparison to P(V) complexes where the oxophillic nature of the lithium atom dominates. All 12 complexes were fully characterized in the solution state by multinuclear NMR spectroscopy. DFT calculations on isomers of monomeric lithiated complex 3 [Ph2PCHC(Me)CH2Li(PMDETA)] described the low energy barrier between transition steps of the subtle delocalization of the allylic chain.

Preparation method of alkyl phosphorylated substances

The invention discloses a preparation method of alkyl phosphorylated substances. According to the invention, alkyl carboxylic acid is used as a starting material, and raw materials are easy to obtain and are various in types. Products prepared by the method disclosed by the invention are various in types and wide in application; and a part of the products can be prepared into important phosphorus ligands and drug key intermediates through simple reduction. In addition, use of high-toxicity phosphine reagents is avoided in the method, the reaction conditions are mild, operation is simple, the yield of the target product is high, pollution is small, and the reaction operation and post-treatment processes are simple, so that the method is suitable for industrial production.

Ni-Catalyzed C-P Coupling of Aryl, Benzyl, or Allyl Ammonium Salts with P(O)H Compounds

A methodology that allows for the construction of C-P bonds via the nickel-catalyzed cross-coupling of organoammonium salts with appropriate phosphorus nucleophiles has been developed. Aryl-, pyridyl-, benzyl-, and allyl-ammonium triflates can be employed as the electrophiles. The employed phosphorus-based nucleophiles included diaryl/dibutyl phosphine oxide, dialkyl phosphonates, and ethyl phenylphosphinate. Functional groups OMe, CN, CF3, F, Cl, C(O)NMe2, and C(O)tBu were tolerated.

Dearylation of arylphosphine oxides using a sodium hydride-iodide composite

A new protocol for the dearylation of arylphosphine oxides was developed using sodium hydride (NaH) in the presence of lithium iodide (LiI). The transient sodium phosphinite could be functionalized with a range of electrophiles in a one-pot fashion.

C-P bond-forming reactions via C-O/P-h cross-coupling catalyzed by nickel

The first Ni-catalyzed C-O/P-H cross-coupling producing organophosphorus compounds is disclosed. This method features wide generality in regard to both C-O and P-H compounds: for C-O compounds, the readily available alcohol derivatives of aryl, alkenyl, benzyl, and allyl are applicable, and for P-H compounds, both >PV(O)H compounds (secondary phosphine oxide, H-phosphinate, and H-phosphonate) and hydrogen phosphines (>PIIIH) can be used as the substrates. Thus, a variety of valuable C(sp2)-P and C(sp3)-P compounds can be readily obtained in good to excellent yields by this new strategy.

Epoxysilanes as substrates in regio- and stereo-specific synthesis of silylated γ-hydroxyphosphane oxides, precursors of stereodefined allylphosphane oxides

Epoxysilanes experienced trans stereospecific α- or β-cleavage by the lithium derivative of methyldiphenylphosphane oxide leading to different compounds. The behaviour of the epoxysilanes towards this nucleophilic reagent depends on the nature of the sily

Some synthetic applications of vinylphosphane oxides

Vinylphosphane oxides have been used as Michael acceptors for the diastereoselective synthesis of anti α-functionalized-β-silylated phosphane oxides and β-stannyl-, β-phenylthio- or β-phosphanyl phosphane oxides. Although the utility of these substrates as dipolarophiles was more limited, we have obtained a mixture of 3- and 4-phosphanylpyrazoles in which the latter is the major regioisomer, by 1,3-cycloaddition with N-phenylsydnone. Moreover, vinylphosphane oxides reacted with aldehydes in the presence of LDA by a Baylis-Hillman type reaction, leading to (E)-β-hydroxyphosphane oxides, which were readily converted in allenes. It is noteworthy that the application of this methodology to silylated substrates has permitted us to synthesize an interesting and more versatile silylallene.

Studies on the efficient generation of phosphorus-carbon bonds via a rearrangement of PIII esters catalysed by trimethylhalosilanes

Halotrimethylsilanes Me3SiX (X = Br, I) catalyse rearrangements of tricoordinate phosphorus esters R′R″P-OR into the corresponding phosphoryl systems R′R″P(O)R. This provides a simple and efficient route to a variety of structures containing phosphorus-carbon bonds, under mild conditions and with good yields. The reaction mechanism was investigated in detail by 31P NMR spectroscopy and independent synthesis of the reaction intermediates. It has been demonstrated that the primary products of this catalytic reaction are halogeno PIII structures R′R″PX and silyl ethers ROSiMe3 and that they subsequently react to give the corresponding phosphorus silyl esters - Me 3SiOPR′R″-and alkyl halides RX. At higher temperatures these intermediates then react to form R′R″P(P)R compounds. This paper also features the surprising observation that when esters Ph 2POR and halotrimethylsilanes Me3SiX (X = Br, I) are used in 2:1 ratio, phosphonium salts Ph2R2P+X - and trimethylsilyl diphenylphosphinate - Ph2P(O) OSiMe3 - are formed as the major products. Experimental evidence indicates that the mechanisms of both reactions are fundamentally different from that of the Michaelis-Arbuzov reaction. Me3SiCl is not reactive and this paper explains why.