Direct conversion of various phosphate sources to a versatile P-X reagent [TBA][PO2X2] via redox-neutral halogenation

Yaling Tian, Dong-ping Chen, Yao Chai, Ming Li, Xi-Cun Wang, Zhengyin Du, Xiaofeng Wu and Zheng-Jun Quan ()
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Yaling Tian: Northwest Normal University
Dong-ping Chen: Northwest Normal University
Yao Chai: Northwest Normal University
Ming Li: Northwest Normal University
Xi-Cun Wang: Northwest Normal University
Zhengyin Du: Northwest Normal University
Xiaofeng Wu: Northwest Normal University
Zheng-Jun Quan: Northwest Normal University

Nature Communications, 2025, vol. 16, issue 1, 1-11

Abstract: Abstract Inorganic phosphates hold significant potential as ideal natural building blocks, forming a fundamental basis for organic and biochemical synthesis. However, their limited solubility, inherent chemical stability, and low reactivity pose substantial challenges to converting phosphates into organophosphates under mild conditions. This study introduces an efficient method for the direct conversion of phosphates into P(V)-X reagents, [TBA][PO2X2] (X = Cl, F), via a redox-neutral halogenation process. This method utilizes cyanuric chloride (or cyanuric fluoride) as the halogenation reagent, in combination with 1-formylpyrrolidine and tetrabutylammonium chloride (TBAC), under ambient conditions. The approach enables effective halogenation conversion for various P(V) sources, including orthophosphates, pyrophosphoric acid, Na3P3O9 and P2O5. Furthermore, we demonstrate the synthetic utility of the P(V)-Cl reagent in the phosphorylation of diverse O-, S-, N- and C-nucleophiles. Key advantages of this conversion process include the use of inexpensive and readily available chemicals, the avoidance of high-energy redox reactions, and the generation of a reactive yet stable P(V)-X reagent.

Date: 2025
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DOI: 10.1038/s41467-025-57255-1

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