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DOI: 10.1055/a-2589-4908
Metal-Free and Scalable Sulfoxide Reduction through the Couple (COCl)2/Et3SiH: Synthesis of Albendazole Hydrochloride
The authors thank the Chemistry Department of Universidad de Los Andes for financial support.

Abstract
Sulfides are valuable organic compounds and important synthetic intermediates. However, the reduction of sulfoxides to sulfides still lacks general applicability due to challenges such as harsh reaction conditions and the reliance on transition metal catalysts. Here, an extension of a previously reported metal-free reduction of sulfoxides is presented, incorporating a greener approach that, in most cases, eliminates the need for chromatographic purification. This method also enabled to scale up the reduction of albendazole to a multigram scale in excellent yield.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2589-4908.
- Supporting Information
Publikationsverlauf
Eingereicht: 24. Februar 2025
Angenommen nach Revision: 16. April 2025
Accepted Manuscript online:
16. April 2025
Artikel online veröffentlicht:
14. Mai 2025
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References
- 1 Kaiser D, Klose I, Oost R, Neuhaus J, Maulide N. Chem. Rev. 2019; 119: 8701
- 2 Poirier GE. Chem. Rev. 1997; 97: 1117
- 3 Yue TJ, Ren WM, Chen L, Gu GG, Liu Y, Lu XB. Angew. Chem. Int. Ed. 2018; 57: 12670
- 4 Wang N, Saidhareddy P, Jiang X. Nat. Prod. Rep. 2020; 37: 246
- 5 Surur AS, Schulig L, Link A. Arch. Pharm. (Weinheim) 2018; 352: 1800248
- 6 Giri P, Gupta L, Naidu S, Joshi V, Patel N, Giri S, Srinivas NR. Drug Metab. Lett. 2018; 12: 101
- 7 Li W, Chen X, Zheng T, Zou Q, Chen W. Chin. J. Org. Chem. 2019; 39: 2443
- 8 Shiri L, Kazemi M. Res. Chem. Intermed. 2017; 43: 6007
- 9 Mitsudome T, Takahashi Y, Mizugaki T, Jitsukawa K, Kaneda K. Angew. Chem. Int. Ed. 2014; 53: 8348
- 10 Yakabe S, Hirano M, Morimoto T. Synth. Commun. 2011; 41: 2251
- 11 Porwal D, Oestreich M. Synthesis 2017; 49: 4698
- 12 Jang Y, Kim KT, Jeon HB. J. Org. Chem. 2013; 78: 6328
- 13 Kong Z, Pan C, Li M, Wen K, Guo W. Green Chem. 2021; 23: 2773
- 14 Zhao J, Luo Z, Liu Y, Chenn S, He J, Xu J, Hu W, Huang Z, Xiong W. Org. Chem. Front. 2023; 10: 5254
- 15 Mo J, Han W, Liu W, Wang W, Zhao J. Chem. Asian J. 2025; 37; e202401807
- 16 Wollein U, Bauer B, Habernegg R, Schramek N. Eur. J. Pharm. Sci. 2015; 77: 100
- 17 Brishty SR, Hossain MJ, Khandaker MU, Faruque MR. I, Osman H, Rahman SM. A. Front. Pharmacol. 2021; 12: 2863
- 18 Abbas A, Newsholme W. Prescriber 2009; 20: 31
- 19 Son DS, Lee ES, Adunyah SE. Immune Netw. 2020; 20: 1
- 20 Chai JY, Jung BK, Hong SJ. Korean J. Parasitol. 2021; 59: 189
- 21 Davis CN, Winters A, Milic I, Devitt A, Cookson A, Brophy PM, Morphew RM. Sci. Rep. 2020; 10: 13445
- 22 Stuchlíková LR, Matoušková P, Vokřál I, Lamka J, Szotáková B, Sečkařová A, Dimunová D, Nguyen LT, Várady M, Skálová L. Int. J. Parasitol. Drugs Drug Resist. 2018; 8: 50
- 23 Alvarez LI, Valladares MM, Canton C, Lanusse CE, Ceballos L. Methods Mol. Biol. 2020; 2137: 213
- 24 Singh R, Bal MS, Singla LD, Kaur P. J. Parasit. Dis. 2017; 41: 463
- 25 Venturina VM, Alejandro MA, Baltazar CP, Abes NS, Mingala CN. Ann. Parasitol. 2015; 61: 283
- 26 Kong Z, Pan C, Li M, Wen L, Guo W. Green Chem. 2021; 23: 2773
- 27 Uematsu T, Ogasawara Y, Suzuki K, Yamaguchi K, Mizuno N. Catal. Sci. Technol. 2017; 7: 1912
- 28 Acosta-Guzmán P, Mahecha-Mahecha C, Gamba-Sánchez D. Chem. Eur. J. 2020; 26: 10348
- 29 Adarve-Cardona L, Gamba-Sánchez D. Processes 2022; 10: 1115
- 30 Bongioanni A, Bueno MS, Abraham-Miranda J, Chattah AK, Ayala AP, Longhi MR, Garnero C. Cryst. Growth Des. 2019; 19: 4538
- 31 Becerra-Cely L, Rueda-Espinosa J, Ojeda-Porras A, Gamba-Sánchez D. Org. Biomol. Chem. 2016; 14: 8474