20187-71-7Relevant academic research and scientific papers
Catalyst- A nd Solvent-Free Hydrophosphorylation of Ketones with Secondary Phosphine Oxides: Green Synthesis of Tertiary α-Hydroxyphosphine Oxides
Afonin, Andrei V.,Gusarova, Nina K.,Ivanova, Nina I.,Khrapova, Kseniya O.,Larina, Lyudmila I.,Pavlov, Dmitry V.,Telezhkin, Anton A.,Trofimov, Boris A.,Volkov, Pavel A.
, p. 2224 - 2232 (2020/08/10)
Tertiary α-hydroxyphosphine oxides have been synthesized via the catalyst- A nd solvent-free reaction between available secondary phosphine oxides and aliphatic, aromatic and heteroaromatic ketones at 20-62? °C in near to 96-98percent yield. The developed method meets the requirements of green chemistry and the PASE (pot, atom, step economy) paradigm. According to quantum-chemical calculations at the B3LYP/6-311++G(d,p) level, the synthesized hydroxyphosphine oxides feature a weak (≈3 kcal·mol -1) O-H···O=P intramolecular hydrogen bond.
Reduction of functionalized tertiary phosphine oxides with BH3
Sowa, Sylwia,Stankevi?, Marek,Szmigielska, Anna,Ma?uszyńska, Hanna,Kozio?, Anna E.,Pietrusiewicz, K. Micha?
, p. 1672 - 1688 (2015/02/19)
A direct stereoselective conversion of tertiary hydroxyalkylphosphine oxides to the corresponding tertiary hydroxyalkylphosphine-boranes involving facile reduction of the P=O bond by BH3 under mild conditions has been developed. The unprecedented facility of reduction of the strong P=O bond by BH3, a mild reducing agent, has been achieved through an intramolecular P=O···B complexation directed by proximal aα- or β-hydroxy groups present in the phosphine oxide structures. As established by two chemical correlations, the developed transformation of hydroxyalkylphosphine oxides into hydroxyalkylphosphine-boranes takes place with complete inversion of configuration at P.
