10.57647/ijc.2026.1601.04

Iron catalysed decarboxylative oxidation photocatalysis of alpha-carbon to access aldehyde/ketone from aryl aliphatic carboxylic acid

  1. Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research-Raebareli, Uttar Pradesh, India.

Received: 2025-08-18

Revised: 2025-10-15

Accepted: 2025-11-04

Published in Issue 2026-03-31

Published Online: 2025-11-25

How to Cite

Katiyar, R., Kumar, S., & Khatik, G. L. (2026). Iron catalysed decarboxylative oxidation photocatalysis of alpha-carbon to access aldehyde/ketone from aryl aliphatic carboxylic acid. Iranian Journal of Catalysis, 16(1 (March 2026). https://doi.org/10.57647/ijc.2026.1601.04

PDF views: 188

Abstract

Carbonyl-containing compounds, such as aldehydes and ketones, are fundamental to synthetic organic chemistry, with wide-ranging applications in the pharmaceutical industry. In this study, we introduce an efficient and streamlined metallophotoredox approach for decarboxylative oxygenation via visible-light-induced ligand-to-metal charge transfer (LMCT). Our method simplifies the transformation of aryl aliphatic carboxylic acids into their corresponding aryl aldehydes and ketones, utilizing iron(III) triflate as a photo catalyst in the presence of TMEDA as a ligand. This strategy not only enhances environmental sustainability but also expands the potential for late-stage functionalization of complex molecules and bioactive compounds.

Keywords

  • Iron (III) triflate, metallophotoredox, decarboxylative oxygenation, carboxylic acid, aldehyde, ketone

References

  1. R. Guan, G. Chen, E.L. Bennett, Z. Huang, J. Xiao, Org. Lett. 25 (2023) 2482–2486. https://doi.org/10.1021/acs.orglett.3c00649.
  2. A. Catalano, A. Mariconda, A.D. Amato, D. Iacopetta, et al. Organics 5 (2024) 395–428. https://doi.org/https://doi.org/10.3390/org5040021.
  3. S. Geng, B. Xiong, Y. Zhang, J. Zhang, Y. He, Z. Feng, Chem. Commun. 55 (2019) 12699–12702. https://doi.org/10.1039/C9CC06584A.
  4. B. Xiong, X. Zeng, S. Geng, S. Chen, Y. He, Z. Feng, Green Chem. 20 (2018) 4521–4527. https://doi.org/10.1039/C8GC02369G.
  5. L.H.M. De Groot, A. Ilic, J. Schwarz, J. Am. Chem. Soc. 145 (2023) 9369–9388. https://doi.org/10.1021/jacs.3c01000.
  6. Y. Pocker, B.C. Davis, J. Am. Chem. Soc. 95 (1973) 6216–6223. https://doi.org/10.1021/ja00800a011.
  7. T.B. Mete, T.M. Khopade, R.G. Bhat, Tetrahedron Lett. 58 (2017) 2822–2825. https://doi.org/10.1016/j.tetlet.2017.06.013.
  8. K. Gholam Reza, A. Roxana, Chem. Res. Chinese Univ. 24 (2008) 464–468. https://doi.org/10.1016/S1005-9040(08)60097-5.
  9. S. Farhadi, P. Zaringhadam, R.Z. Sahamieh, Tetrahedron Lett. 47 (2006) 1965–1968. https://doi.org/10.1016/j.tetlet.2006.01.082.
  10. M. Araghi, F. Bokaei, Polyhedron 53 (2013) 15–19. https://doi.org/10.1016/j.poly.2013.01.052.
  11. Y. Sakakibara, P. Cooper, K. Murakami, K. Itami, Chem. - An Asian J. 13 (2018) 2410–2413. https://doi.org/10.1002/asia.201800529.
  12. T.M. Faraggi, W. Li, D.W.C. MacMillan, Isr. J. Chem. 60 (2020) 410–415. https://doi.org/10.1002/ijch.201900130.
  13. S. Shirase, S. Tamaki, K. Shinohara, K. Hirosawa, et al. J. Am. Chem. Soc. 142 (2020) 5668–5675. https://doi.org/10.1021/jacs.9b12918.
  14. J.L. Tu, H. Gao, M. Luo, L. Zhao, C. Yang, L. Guo, W. Xia, Green Chem. 24 (2022) 5553–5558. https://doi.org/10.1039/d2gc01738e.
  15. F.N. Castellano, J. Rehbein, O. Reiser, ChemComm 58 (2022) 4456–4459. https://doi.org/10.1039/d2cc00570k.
  16. R. Bashary, G.L. Khatik, Bioorg. Chem. 82 (2019) 156–162. https://doi.org/10.1016/j.bioorg.2018.10.010.
  17. L. Chandrakar, R. Ambatwar, G.L. Khatik, J. Mol. Struct. 1296 (2024) 136817. https://doi.org/https://doi.org/10.1016/j.molstruc.2023.136817.
  18. S. Kumar, N. Bhanwala, J. Malik, K. Jagrati, G.L. Khatik, Res. Chem. Intermed. 50 (2024) 4387–4405. https://doi.org/10.1007/s11164-024-05360-z.
  19. M. Devi, P. Kumar, et al. Eur. J. Med. Chem. 250 (2023) 115230. https://doi.org/https://doi.org/10.1016/j.ejmech.2023.115230.
  20. V. Gupta, N.S. Sundaramoorthy, et al. J. Comput. Biophys. Chem. 23 (2024) 1197–1208. https://doi.org/10.1142/S2737416524500388.
  21. N. Bhanwala, N.S. Sundaramoorthy, et al. Med. Chem. Res. 33 (2024) 1926–1937. https://doi.org/10.1007/s00044-024-03295-z.
  22. L. Ellouzi, I., Regraguy, B., El Hajjaji, et al. Iran. J. Catal. 12 (2011). https://doi.org/https://doi.org/10.30495/ijc.2022.1941684.1875.
  23. M. Innocent, G. Lalande, et al. European J. Org. Chem. 26 (2023) e202300892. https://doi.org/10.1002/ejoc.202300892.