AgNO₃/K₂S₂O₈-Promoted Decarboxylative Oxyphosphorylation of Cinnamic Acids: A Mild Synthesis of β-Ketophosphonates

Abstract

This works reports an efficient and general method for synthesizing β-ketophosphonate derivatives using AgNO₃ as the catalyst and K₂S₂O₈ as the oxidant under mild conditions (room temperature and open-air atmosphere). The procedure is effective under simple and very convenient conditions with easy isolation and purification of the product. Potassium persulfate (K₂S₂O₈) has emerged as a cost-effective, easily accessible inorganic oxidant. K₂S₂O₈ exhibited a unique utility as the most efficient oxidant due to its greater solubility in organic media. A broad substrate scope and suitable functional group compatibility were observed. Experimental studies show that the reaction undergoes a radical process.

Keywords

β-Ketophosphonates - Decarboxylative oxyphosphorylation - C–P bond formation - AgNO₃ catalysis - K₂S₂O₈ oxidant - Radical mechanism - Cinnamic acids - Dialkyl phosphites

Author Contributions

D.V.: Conceptualization, Methodology, Writing – review & editing, Funding acquisition, Supervision. A.P.: Conceptualization, Methodology, Writing – review & editing, Funding acquisition. V.K.Y.: Conceptualization, Methodology, Writing – review & editing. A.V.: Conceptualization, Methodology, Investigation, Writing- Original draft preparation. G.C.: Conceptualization, Methodology, Investigation, Writing- Original draft preparation. M.D.: Methodology, Investigation, Writing-Original draft preparation. B.M.: Methodology, Investigation.

Data availability

The data that support the findings of this study are available from the corresponding author upon reasonable request.

Publication History

Received: 15 November 2025

Accepted after revision: 10 February 2026

Article published online:
04 March 2026

• References

• 1 McManus HA, Guiry PJ. Chem Rev 2004; 104: 4151-4202
• 2 Spampinato V, Tuccitto N, Quici S. et al. Langmuir 2010; 26: 8400-8406
• 3 Kumar TS, Zhou SY, Joshi BV. et al. J Med Chem 2010; 53: 2562-2576
• 4 Mikołajczyk M. Pure Appl Chem 2019; 91: 811-838
• 5 Cioni JP, Doroghazi JR, Ju KS. et al. J Nat Prod 2014; 77: 243-249
• 6 Hecker SJ, Erion MD. J Med Chem 2008; 51: 2328-2345
• 7 Tripolszky A, Tóth E, Szabó PT. et al. Molecules 2020; 25: 2643
• 8 Assiri MA, Ali TE, Ali MM, Yahia IS. Phosphorus Sulfur Silicon Relat Elem 2018; 193: 668-674
• 9 Gibadullina E, Nguyen TT, Strelnik A. et al. Eur J Med Chem 2019; 184: 111735
• 10 Keough DT, Hockova D, Holy A. et al. J Med Chem 2009; 52: 4391-4399
• 11 Zhou SF, Li DP, Liu K, Zou JP, Asekun OT. J Org Chem 2015; 80: 1214-1220
• 12 Perumal SK, Adediran SA, Pratt RF. Bioorg Med Chem 2008; 16: 6987-6994
• 13 Gu J, Cai C. Org Biomol Chem 2017; 15: 4226-4230
• 14 McCabe DJ, Duesler EN, Paine RT. Inorg Chem 1985; 24: 4626-4629
• 15 Chen X, Li X, Chen XL. et al. Chem Commun 2015; 51: 3846-3849
• 16 Bhattacharya AK, Thyagarajan G. Chem Rev 1981; 81: 415-430
• 17 Wei W, Ji JX. Angew Chem Int Ed 2011; 50: 9097-9099
• 18 Li X, Hu G, Luo P. et al. Adv Synth Catal 2012; 354: 2427-2432
• 19 Xiang J, Yi N, Wang R. et al. Tetrahedron 2015; 71: 694-699
• 20 Xie L, Yuan R, Wang R, Peng Z, Xiang J, He W. Eur J Org Chem 2014; 2014: 2668-2671
• 21 Zhou P, Hu B, Li L, Rao K, Yang J, Yu F. J Org Chem 2017; 82: 13268-13276
• 22 Zhou M, Chen M, Zhou Y. et al. Org Lett 2015; 17: 1786-1789
• 23 Xiong B, Si L, Zhu L. et al. J Org Chem 2023; 88: 12502-12518
• 24 Mandal S, Bera T, Dubey G, Saha J, Laha JK. ACS Catal 2018; 8: 5085-5144
• 25 Xiang CB, Bian YJ, Mao XR, Huang ZZ. J Org Chem 2012; 77: 7706-7710
• 26 Pandey VK, Tiwari CS, Rit A. Chem Asian J 2022; 17: e202200703
• 27 Zhao WM, Chen XL, Yuan JW, Qu LB, Duan LK, Zhao YF. Chem Commun 2014; 50: 2018-2020