15374-44-4

Usage

Uses

Used in Organometallic Chemistry:
(naphthalen-1-ylmethyl)(diphenyl)phosphane oxide is used as a ligand for [forming coordination complexes with various metal atoms] because of its ability to coordinate with a wide range of metal atoms, making it a versatile tool in organometallic chemistry.
Used in Catalysis:
It is used as a catalyst or a catalyst component in [various catalytic reactions] due to its potential to enhance the efficiency and selectivity of these reactions.
Used in Synthesis of Phosphorus-Containing Compounds:
(naphthalen-1-ylmethyl)(diphenyl)phosphane oxide is used as a precursor in the synthesis of [other phosphorus-containing compounds], taking advantage of its unique structure and reactivity.
Used in Chemical Synthesis:
(naphthalen-1-ylmethyl)(diphenyl)phosphane oxide is also used in the design and synthesis of new chemical compounds, serving as a valuable building block for creating novel molecules with specific properties and applications.

Upstream product

• 86-55-5 1-naphthalenecarboxylic acid 
• 4559-70-0 Diphenylphosphine oxide 
• 879-18-5 naphthalene-1-carbonic acid chloride 
• 36773-67-8 1-naphthoic acid,phenyl ester 
• 16413-71-1 N,N-dimethyl(naphthalen-1-yl)methanamine 
• 86-52-2 1-Chloromethylnaphthalene 

Downstream Products

• 94257-46-2 1-Phenyl-2-naphthyl-⁽¹⁾-cyclopropan 
• 1507379-40-9 ((naphthalen-1-yl)(phenyl)methyl)diphenylphosphine oxide 

Relevant academic research and scientific papers

Controllable phosphorylation of thioesters: Selective synthesis of aryl and benzyl phosphoryl compounds

The controllable phosphorylations of thioesters were developed. When the reaction was catalyzed by a palladium catalyst, aryl or alkenyl phosphoryl compounds were generated through decarbonylative coupling, while the benzyl phosphoryl compounds were produced through deoxygenative coupling when the reaction was carried out in the presence of only a base.

Catalytic Deoxygenative Coupling of Aromatic Esters with Organophosphorus Compounds

We have developed a deoxygenative coupling of aromatic esters with diarylphosphine oxides/dialkyl phosphonates under palladium catalysis. In this reaction, aromatic esters can work as novel benzylation reagents to give the corresponding benzylic phosphorus compounds. The key of this reaction is the use of phenyl esters, an electron-rich diphosphine as a ligand, and sodium formate as a hydrogen source. Arylcarboxylic acids were also applicable in this reaction using (Boc)2O as an additive. Palladium/dcype worked to activate the acyl C-O bond of the ester and to support the reduction with sodium formate.

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.

Palladium-catalyzed benzylic substitution of benzyl carbonates with phosphorus nucleophiles

A wide range of benzyl carbonates reacted with dimethyl phosphonate or diphenylphosphine oxide in the presence of the palladium catalyst, [Pd(η3-allyl)Cl]2DPEphos, to give dimethyl benzylphosphonates and benzyldiphenylphosphine oxides in high yields. The catalytic phosphonylation was applied to the one-pot synthesis of alkenes from the benzyl esters.

Palladium-catalyzed α-arylation of benzylic phosphine oxides

A novel approach to prepare diarylmethyl phosphine oxides from benzyl phosphine oxides via deprotonative cross-coupling processes (DCCP) is reported. The optimization of the reaction was guided by High-Throughput Experimentation (HTE) techniques. The Pd(OAc)2/Xantphos-based catalyst enabled the reaction between benzyl diphenyl or dicyclohexyl phosphine oxide derivatives and aryl bromides in good to excellent yields (51-91%).