Straightforward Superbase-Mediated Reductive O-Phosphorylation of Aromatic and Heteroaromatic Ketones with Red Phosphorus in the Superbase Suspension KOH/DMSO(H<sub>2</sub>O)

Straightforward Superbase-Mediated Reductive O-Phosphorylation of Aromatic and Heteroaromatic Ketones with Red Phosphorus in the Superbase Suspension KOH/DMSO(H<sub>2</sub>O)

It was shown for the first time that diaryl(hetaryl)ketones are capable of directly phosphorylating with red phosphorus in the superbase suspension KOH/DMSO(H<sub>2</sub>O) at 85 °C for 1.5 h to afford potassium bis(diaryl(hetaryl)methyl)phosphates that were earlier inaccessible in a yie...

Full description

Saved in:
Bibliographic Details
Main Authors: Vladimir A. Kuimov, Svetlana F. Malysheva, Natalia A. Belogorlova, Ruslan I. Fattakhov, Alexander I. Albanov, Irina Yu. Bagryanskaya, Nikolay I. Tikhonov, Boris A. Trofimov
Format: Article
Language:English
Published: MDPI AG 2025-03-01
Series:Molecules
Subjects:
red phosphorus
strong base
bis(benzhydryl)phosphates
benzophenone
single-electron transfer
Online Access:https://www.mdpi.com/1420-3049/30/6/1367
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:It was shown for the first time that diaryl(hetaryl)ketones are capable of directly phosphorylating with red phosphorus in the superbase suspension KOH/DMSO(H<sub>2</sub>O) at 85 °C for 1.5 h to afford potassium bis(diaryl(hetaryl)methyl)phosphates that were earlier inaccessible in a yield of up to 45%. The ESR data demonstrate that unlike previously published phosphorylation with elemental phosphorus, this new phosphorylation reaction proceeds via a single electron transfer from polyphospide anions to diaryl(hetaryl)ketones. This is the first example of the C-O-P bond generation during the phosphorylation with elemental phosphorus in strongly basic media, which usually provides C-P bond formation.
ISSN:1420-3049

Similar Items