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Transition-metal-free Amination Phosphoryl Azide for the Synthesis of Phosphoramidates

Overview
Journal RSC Adv
Specialty Chemistry
Date 2022 May 6
PMID 35521381
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Abstract

A facile and efficient approach to phosphoramidates was developed amination of phosphoryl azides. A variety of phosphoramidates were obtained in one step with good to excellent yields under a mild reaction system. The process uses easily available amines as a N source and offers a new opportunity for P-N bond formation.

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References
1.
Berridge M, Irvine R . Inositol phosphates and cell signalling. Nature. 1989; 341(6239):197-205. DOI: 10.1038/341197a0. View

2.
Guijarro J, Baleux F, San Millan J, Castilla M, Rico M, Moreno F . Chemical structure and translation inhibition studies of the antibiotic microcin C7. J Biol Chem. 1995; 270(40):23520-32. DOI: 10.1074/jbc.270.40.23520. View

3.
Wittine K, Benci K, Rajic Z, Zorc B, Kralj M, Marjanovic M . The novel phosphoramidate derivatives of NSAID 3-hydroxypropylamides: synthesis, cytostatic and antiviral activity evaluations. Eur J Med Chem. 2008; 44(1):143-51. DOI: 10.1016/j.ejmech.2008.03.037. View

4.
Bialy L, Waldmann H . Inhibitors of protein tyrosine phosphatases: next-generation drugs?. Angew Chem Int Ed Engl. 2005; 44(25):3814-39. DOI: 10.1002/anie.200461517. View

5.
Pan C, Jin N, Zhang H, Han J, Zhu C . Iridium-catalyzed phosphoramidation of arene C-H bonds with phosphoryl azide. J Org Chem. 2014; 79(19):9427-32. DOI: 10.1021/jo5018052. View