24442-45-3Relevant academic research and scientific papers
MW-Assisted P-C Coupling Reaction Using P-Ligand-Free Pd(OAc) 2 Catalyst
Jablonkai, Erzsébet,Balázs, László B.,Keglevich, Gy?rgy
, p. 660 - 663 (2015/07/20)
P-C coupling reactions of a variety of >P(O)H species with aryl bromides were found to take place under P-ligand-free microwave conditions.
A "green" variation of the Hirao reaction: The P-C coupling of diethyl phosphite, alkyl phenyl-H-phosphinates and secondary phosphine oxides with bromoarenes using a P-ligand-free Pd(OAc)2 catalyst under microwave and solvent-free conditions
Keglevich, Gyoergy,Jablonkai, Erzsebet,Balazs, Laszlo B.
, p. 22808 - 22816 (2014/06/23)
The P-C coupling of diethyl phosphite, alkyl phenyl-H-phosphinates, diphenylphosphine oxide and dialkylphosphine oxides with bromoarenes may be performed in the presence of a P-ligand-free Pd(OAc)2 catalyst and triethylamine under microwave-assisted (MW) and, in almost all cases, solvent-free conditions to afford diethyl arylphosphonates, alkyl diphenylphosphinates, aryldiphenylphosphine oxides and dialkylphenylphosphine oxides, respectively. This is the "greenest" accomplishment of the well-known Hirao reaction that has now been found to have general application for a broad spectrum of >P(O)H species with different reactivity and a great variety of substituted bromobenzenes. The alkyl phenyl-H-phosphinates were prepared by the MW-promoted alkylation of phenyl-H-phosphinic acid in the absence of any solvent. This journal is the Partner Organisations 2014.
Sodium in liquid ammonia - A versatile tool in modifications of arylphosphine oxides
Stankevi?, Marek,W?odarczyk, Adam,Jaklińska, Magdalena,Parcheta, Renata,Pietrusiewicz, K. Micha?
experimental part, p. 8671 - 8678 (2011/12/03)
A simple and practical method for modifications of tertiary arylphosphine oxides based on their reaction with sodium in liquid ammonia is presented. Depending on the structure of the starting compounds, either dearomatisation of the phenyl substituent or cleavage of a P-aryl bond from phosphorus atom can be selectively performed and the corresponding (1,4-cyclohexadien-3-yl)phosphine oxides or secondary phosphine oxides were obtained in good to excellent yields.
Formation and Reactions of Diorganophosphinite Ions in Liquid Ammonia. Synthesis of Triorganophosphine Oxides by the SRN1 Mechanism
Bornancini, Estaban R. N.,Rossi, Roberto A.
, p. 2332 - 2336 (2007/10/02)
The reaction of triphenyl- and tribenzylphosphine oxides with alkali metals in liquid ammonia gave diphenyl- and dibenzylphosphinite ions, respectively, in high yields and a small amount of deoxygenated products.These ions reacted under photostimulation with aryl halides by the SRN1 mechanism to give aryldiphenyl- and aryldibenzylphosphine oxides in good yields.With tribenzylphosphine oxide, by consecutive debenzylation with alkali metals followed by photostimulated reaction with aryl halides, all the benzylic moieties could be replaced by aromatic moieties to finally obtain unsymmetrical triarylphosphine oxides.
Three-membered Ring Heterocycles, 14. α-Halogenation of Tertiary Phosphane Oxides
Heuschmann, Manfred,Quast, Helmut
, p. 3384 - 3401 (2007/10/02)
The symmetrically substituted tertiary phosphane oxides 5 were obtained from phosphorus halides 4 and 6 using organometallic reagents.Dibenzylphenylphosphane oxide (5c) reacted with bromine at 150 deg C to give all three possible diastereomeric α,α'-dibromophosphane oxides. e.g. (R,R/S,S)-2c, (r)-2c, and (s)-2c, and one α-bromophosphane oxide 8.The phosphane oxides 5a, b, d were lithiated once or twice in the α-positions by means of butyllithium.The α,α'-dilithiophoasphane oxides -5 reacted with tetrachloromethane below -80 deg C to yield the α-chlorophosphane oxides 1c - e whose diastereomeric ratios were controlled kinetically.The thermodynamically controlled ratios were adjusted with bases.While the α-lithiated dineopentyl phosphane oxides -5a and -5d also afforded the α-chlorophosphane oxides 1c and 1d, respectively, with an excess of tetrachloromethane, the α,α-dichlorophosphane oxide 9 was formed from the α-lithiobenzylphosphane oxide 5b.This difference is attributed to the acidity of the α-protons and steric factors.The configurations and preferred conformations of the α,α'-dibromophosphane oxides 2c and the α-chlorophosphane oxides 1c - e were determined on the basis of the 1H-31P coupling of the methine protons.
