73207-71-3Relevant academic research and scientific papers
Alcohol-based Michaelis-Arbuzov reaction: An efficient and environmentally-benign method for C-P(O) bond formation
Ma, Xiantao,Xu, Qing,Li, Huan,Su, Chenliang,Yu, Lei,Zhang, Xu,Cao, Hongen,Han, Li-Biao
supporting information, p. 3408 - 3413 (2018/08/06)
The famous Michaelis-Arbuzov reaction is extensively used both in the laboratory and industry to manufacture tons of widely-used organophosphoryl compounds every year. However, this method and the modified Michaelis-Arbuzov reactions developed recently still have some limitations. We now report a new alcohol-version of the Michaelis-Arbuzov reaction that can provide an efficient and environmentally-benign method to address the problems of the known Michaelis-Arbuzov reactions. That is, a wide range of alcohols can readily react with phosphites, phosphonites, and phosphinites to give all the three kinds of phosphoryl compounds (phosphonates, phosphinates, and phosphine oxides) using an n-Bu4NI-catalyzed efficient C-P(O) bond formation reaction. This general method can also be easily scaled up and used for further synthetic transformations in one pot.
Dearylation of arylphosphine oxides using a sodium hydride-iodide composite
Tejo, Ciputra,Pang, Jia Hao,Ong, Derek Yiren,Oi, Miku,Uchiyama, Masanobu,Takita, Ryo,Chiba, Shunsuke
supporting information, p. 1782 - 1785 (2018/02/21)
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.
Palladium-catalyzed benzylic substitution of benzyl carbonates with phosphorus nucleophiles
Makida, Yusuke,Usui, Kazumi,Ueno, Satoshi,Kuwano, Ryoichi
supporting information, p. 1814 - 1817 (2017/11/23)
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.
Extraction of rare-earth elements(III) from nitric acid solutions with bis(diarylphosphorylmethyl)benzenes
Turanov,Karandashev,Baulin,Kirillov,Kirillov,Rychkov,Tsivadze
, p. 1015 - 1021 (2015/08/18)
Abstract Extraction of micro quantities of rare-earth elements(III) from HNO3 solutions as complexes with bis(diarylphosphorylmethyl)benzenes depending on the nature of organic diluent and HNO3 concentration in equilibrium aqueous ph
Room temperature, palladium-mediated P-arylation of secondary phosphine oxides
Bloomfield, Aaron J.,Herzon, Seth B.
supporting information, p. 4370 - 4373 (2012/10/29)
We show that a broad range of aryl iodides are efficiently coupled with secondary phosphine oxides using 1 mol % of a catalyst formed in situ from tris(dibenzylideneacetone)dipalladium and Xantphos (1). Scalemic (S)-methylphenylphosphine oxide [(S)-2e] is shown to undergo arylation without detectable stereoerosion. The application of this method to the synthesis of novel P-chiral phosphines and PCP ligands is demonstrated.
A recyclable perfluoroalkylated PCP pincer palladium complex
Duncan, Daniel,Hope, Eric G.,Singh, Kuldip,Stuart, Alison M.
experimental part, p. 1998 - 2005 (2011/04/15)
A new fluorous PCP pincer ligand has been coordinated to Ni(ii), Pd(ii) and Pt(ii). The air stable palladium complex, which promotes Heck reactions between methyl acrylate and either aryl bromides or iodides, can be recovered intact by fluorous solid-phase extraction and was reused four times in the Heck reaction between methyl acrylate and 4-bromoacetophenone without loss in catalytic activity. The Royal Society of Chemistry 2011.
Ionic-liquid-promoted Michaelis-Arbuzov rearrangement
Matveeva,Odinets,Kozlov,Shaplov,Mastryukova
, p. 7645 - 7648 (2007/10/03)
Room-temperature imidazolium ionic liquids, [Rmim][X], proved to be environmentally benign recyclable solvents promoting the Michaelis-Arbuzov rearrangement, which can be performed even at room temperature in a short period of time. The best ionic liquid of choice depended on the starting phosphorus(III) ester, namely, for triethyl phosphite [bmim][NTf2] demonstrated better results while for ethyl diphenylphosphinite it was [hmim][Br].
Using polarization effects to alter chemical reactivity: A simple host which enhances amine nucleophilicity
Ashton, Peter R.,Calcagno, Patrizia,Spencer, Neil,Harris, Kenneth D. M.,Philp, Douglas
, p. 1365 - 1368 (2007/10/03)
(Matrix Presented) The rational design of a bis(phosphine oxide) host which is capable of binding a benzylic amine is presented. The ability of this host to increase the rate of addition of 4-fluorobenzylamine to N-phenylmaleimide is rationalized in terms of the enhancement of the nucleophilicity of the benzylic amine.
