95704-99-7

Upstream product

• 31106-82-8 2-(bromomethyl)pyridine hydrobromide 
• 13119-80-7 (α-pyridylmethyl)diphenylphosphine oxide 
• 55401-97-3 2-(Bromomethyl)pyridine 
• 100-58-3 phenylmagnesium bromide 
• 4377-33-7 2-chloromethylpyridine 
• 4559-70-0 Diphenylphosphine oxide 
• 13341-40-7 (E)-1,2-bis(2-pyridyl)ethene 

Downstream Products

• 1449196-51-3 C₂₆H₂₉ErN₅O₁₂P*CH₂Cl₂ 
• 1449196-43-3 2-[1-(diphenylphosphinoyl)-1-(1-oxy-pyridin-2yl)-methyl]pyridine N-oxide 

Relevant academic research and scientific papers

Boron Lewis Acid-Catalyzed Hydrophosphinylation of N-Heteroaryl-Substituted Alkenes with Secondary Phosphine Oxides

We report the boron-catalyzed hydrophosphinylation of N-heteroaryl-substituted alkenes with secondary phosphine oxides that furnishes various phosphorus-containing N-heterocycles. This process proceeds under mild conditions and enables the introduction of a phosphorus atom into multisubstituted alkenylazaarenes. The available mechanistic data can be explained by a reaction pathway wherein the C-P bond is created by the reaction between the activated alkene (by coordination to a boron catalyst) and the phosphorus(III) nucleophile (in tautomeric equilibrium with phosphine oxide).

Synthesis and properties of new (Phosphinoylmethyl)pyridine N-oxides

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