Catalyst- and Solvent-Free Hydrophosphorylation of Ketones with Secondary Phosphine Oxides: Green Synthesis of Tertiary α-Hydroxyphosphine Oxides

Nina K. Gusarova; Nina I. Ivanova; Kseniya O. Khrapova; Pavel A. Volkov; Anton A. Telezhkin; Lyudmila I. Larina; Andrei V. Afonin; Dmitry V. Pavlov; Boris A. Trofimov

doi:10.1055/s-0040-1707945

Synthesis, Table of Contents

Synthesis 2020; 52(15): 2224-2232
DOI: 10.1055/s-0040-1707945

paper

Catalyst- and Solvent-Free Hydrophosphorylation of Ketones with Secondary Phosphine Oxides: Green Synthesis of Tertiary α-Hydroxyphosphine Oxides

Nina K. Gusarova

,

Nina I. Ivanova

,

Kseniya O. Khrapova

,

Pavel A. Volkov

,

Anton A. Telezhkin

,

Lyudmila I. Larina

,

Andrei V. Afonin

,

Dmitry V. Pavlov

,

Boris A. Trofimov∗

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Email: boris_trofimov@irioch.irk.ru

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Abstract

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Abstract

Tertiary α-hydroxyphosphine oxides have been synthesized via the catalyst- and solvent-free reaction between available secondary phosphine oxides and aliphatic, aromatic and heteroaromatic ketones at 20–62 °C in near to 96–98% 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.

Key words

ketones - secondary phosphine oxides - catalyst- and solvent-free addition - α-hydroxyphosphine oxides

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References

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