13119-80-7Relevant academic research and scientific papers
Catalytic Deoxygenative Coupling of Aromatic Esters with Organophosphorus Compounds
Kurosawa, Miki B.,Isshiki, Ryota,Muto, Kei,Yamaguchi, Junichiro
supporting information, p. 7386 - 7392 (2020/04/30)
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.
Copper(II) Acetate-Catalyzed Synthesis of Phosphorylated Pyridines via Denitrogenative C?P Coupling between Pyridotriazoles and P(O)H Compounds
Shen, Ruwei,Dong, Chao,Yang, Jianlin,Han, Li-Biao
supporting information, p. 4252 - 4258 (2018/10/02)
A new inexpensive copper-catalyzed denitrogenative C?P coupling reaction of pyridotriazoles with P(O)H compounds has been developed. The reaction proceeds via a process of copper-catalyzed P(O)?H insertion into the pyridyl carbene intermediates generated in situ from pyridotriazoles. This reaction provides a new and effective method for the synthesis of a variety of 2-picolylphosphoryl compounds. (Figure presented.).
Synthesis and properties of new (Phosphinoylmethyl)pyridine N-oxides
Pailloux, Sylvie L.,Rosario-Amorin, Daniel,Chakravarty, Manab,Camus, Jean-Michel,Smith, Karen Ann,Duesler, Eileen N.,Dickie, Diane A.,Paine, Robert T.,Klausmeyer, Kevin K.,Padron, Daniel A.,Hay, Benjamin P.,Delmau, Laetitia H.
, p. 1101 - 1116 (2013/07/27)
Syntheses for 2-[1-(diarylphosphinoyl)-1-(pyridin-2-yl)methyl]pyridines, (8a, b), and 2-[1-(diarylphosphinoyl)-1, 1-bis(methylpyridin-2yl)methyl] pyridines, (11a, b), (Ar = C6H5 and 2-CF3C 6H4), based on substitution of 2-methylpyridine fragments onto the exo methylene carbon atom of 2-[(diaryl)phosphinoylmethyl]pyridine platforms, are described. N-oxidations of 8a, b and 11a, b produced the 2-[1-(diarylphosphinoyl)-1-(1-oxy-pyridin-2yl)methyl]pyridine N-oxides (5a, b) and the 2-[1-(diarylphosphinoyl)-1, 1-bis(1-oxy-methylpyridin-2-yl)methyl] pyridines (6a, b), respectively. The short-arm pyridine fragment of 11a, b resists N-oxidation, and the fully oxidized molecules, 2-[1-(diarylphosphinoyl)-1, 1-bis(1-oxy-methylpyridin-2-yl)methyl]pyridine N-oxides (7a, b) were not isolated. Molecular mechanics calculations for gas phase 1:1 ligand/lanthanide complexes indicated that 5a should accommodate a tridentate NO(meNO)PO coordination mode with minimal steric strain. In contrast, 7a cannot form tetradentate NO(meNO)2PO chelates; however, tridentate binding should be accessible with minimal ligand strain. Coordination complexes of 8a, b, 5a, b, 6a, b and 11a, b with Ln(NO3)3 salts were isolated and a X-ray crystal structure for [Er(8a)(NO 3)3(MeOH)2]·CH2Cl 2, revealed a monodentate Er-O=P interaction. On the other hand, complexes formed by a more symmetrical trifunctional phenylphosphino-bis-2- methylpyridine N, N, P-trioxide ligand, (meNO)2PO*, {La[(meNO)2PO*)](OTf)2(MeOH)3(H 2O)+}(OTf-) and {Pr[(meNO)2PO* )](OTf)(MeOH)4+}(OTf-)2, realized a tridentate coordination mode. Solvent extraction behaviors for EuIII and AmIII in nitric acid solutions using 5a, b, 6a, b, Ph 3PO and the parent bifunctional ligand 2-[(diphenylphosphanyl)methyl] pyridine N, P-dioxide (3a) in 1, 2-dichloroethane were assessed, and 5a, b and 6a, b were found to behave more like Ph3PO than 3a. Copyright
PHOSPHORYLMETHYLPYRIDINES AND THEIR n-OXIDES: SYNTHESIS AND EQUILIBRIUM CH-ACIDITY
Bodrin, G. V.,Matveeva, A. G.,Terekhova, M. I.,Matrosov, E. I.,Petrov, E. S.,et al.
, p. 810 - 818 (2007/10/02)
Certain phosphorylmethylpyridines and their N-oxides were synthesized, which are of interest as extractants and complex-forming agents.Their equilibrium CH-acidity with reference to 9-phenylfluorene (k+ counterion) was studied by the indicator method in dimethyl sulfoxide.The acidifying action of a series of pyridine groupings was characterized by means of ?C- values.
