Preparation of Alkyl N -Alkylphosphonamidates by the Microwave-Assisted Selective Monoaminolysis of Dialkyl Phosphites

Abstract The title compounds, (RO)(NHR′)P(O)H, were synthesized earlier from P-chloro intermediates by substitutions or from dialkyl phosphites by reaction with organometallic reagents. Instead of these not clear-cut and not efficient transformations, a green, solvent- and catalyst-free synthesis of alkyl phosphonamidates has been developed by the microwave-assisted aminolysis of dialkyl phosphites. The monosubstitution was fully selective. Under more forcing conditions, an interesting side reaction was observed. The resulting products may be valuable reagents to prepare α-hydroxy- and α-aminophosphonic derivatives.

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Publication Details

Journal
Organic Letters
Published
2026-09-09
DOI
https://doi.org/10.1021/acs.orglett.6c03484
Primary Topic
Organophosphorus compounds synthesis
Type
article
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article

Preparation of Alkyl N -Alkylphosphonamidates by the Microwave-Assisted Selective Monoaminolysis of Dialkyl Phosphites

Péter Keglevich, Zsuzsanna Szalai, György Keglevich, Anna Sára Kis
Organic Letters
Organophosphorus compounds synthesis
article

Preparation of Alkyl N -Alkylphosphonamidates by the Microwave-Assisted Selective Monoaminolysis of Dialkyl Phosphites

Péter Keglevich, Zsuzsanna Szalai, György Keglevich, Anna Sára Kis
article en

Abstract

Abstract The title compounds, (RO)(NHR′)P(O)H, were synthesized earlier from P-chloro intermediates by substitutions or from dialkyl phosphites by reaction with organometallic reagents. Instead of these not clear-cut and not efficient transformations, a green, solvent- and catalyst-free synthesis of alkyl phosphonamidates has been developed by the microwave-assisted aminolysis of dialkyl phosphites. The monosubstitution was fully selective. Under more forcing conditions, an interesting side reaction was observed. The resulting products may be valuable reagents to prepare α-hydroxy- and α-aminophosphonic derivatives.

Organic Letters
Budapest University of Technology and Economics (HU)
Clean water and sanitation
Openalex Percentile: Top 20%
Organophosphorus compounds synthesis
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