A NEW REAGENT FOR SYNTHESIS OF NITRILES FROM ALDOXIMES USING ALUMINIUM (III) TRIFLATE

Authors

DOI:

https://doi.org/10.24193/subbchem.2025.4.06

Keywords:

Aluminum triflate, Nitriles, Reaction mechanism, Catalysis, Dehydration

Abstract

We report a new, highly efficient, and straightforward method for the dehydration of aldoximes to nitriles using aluminium (III) triflate [Al(OTf)3] as a catalyst in acetonitrile. This one-step transformation proceeds with moderate to excellent yields (44–94%) and tolerates a wide range of substrates, including those with aromatic, functionalized aryl, heteroaryl, alkyl, and cycloalkyl moieties. This approach serves as a practical method for the synthesis of nitriles from aldoximes, yielding valuable synthetic intermediates for the pharmaceutical and agrochemical industries. In addition, the method's operational simplicity and the convenient isolation of the final product are its key advantages.

References

1. M. Sundermeier; A.Zapf; M. Beller M; J. Sans; Tetrahedron Lett., 2001, 42, 6707-6710.

2. F. Santos; S. Esther; F. S. C. Juan; P. Julio P; A. Amparo; Chem. Comm., 2003, 844-845.

3. P. Hu; J. Chai; Y. Duan; Z. Liu; G. Gui; L. Chen; J. Mater. Chem., A 2016, 4, 10070-10083.

4. E. Pascual E; F. Sivera F; U. Yasothan; P. Kirkpatrick; Nat. Rev. Drug. Discov., 2009, 8, 191-192.

5. F. F. Fleming; L. Yao; P. C. Ravikumar; B. L. Funk; C. Shook; J. Med. Chem., 2010, 53, 7902-7917.

6. J. Gurjar; J. Bater; V. V. Fokin; Chem. Eur. J., 2019, 25, 1906-1909.

7. Y. Zhang; W. Li; Z. Hu; X. Jing; L. Yu; Chin. Chem. Lett., 2024, 35, 108938.

8. F. Wang; C. Yang; Y. Shi; L. Yu; Mol. Catal., 2021, 514, 11849.

9. J. A. Campbell; G. McDougald; H. McNab; L. V. C. Rees; R. G. Tyas; Synthesis, 2007, 3179-3184.

10. M. K. Sing; M. K. Lakshman; J. Org. Chem., 2009, 74, 3079-3084.

11. L. D. S. Yadav; V. P. Srivastava; R. Patel; Tetrahedron Lett., 2009, 50, 5532-5535.

12. A. Rai A; L. D. S. Yadav; Eur. J. Org. Chem., 2013, 10, 1889-1893.

13. N. Uludag; Org. Prep. Proced. Int., 2024, 56, 516-522.

14. O. Asutay; N. Hamarat; N. Uludag; N. Coskun; Tetrahedron Lett., 2015, 56, 3902-3904.

15. N. Uludag; Russ J. Org. Chem., 2020, 56, 1640-1645.

16. N. Uludag; O. N. Giden; Rev. Roum. Chim., 2019, 64, 993-998.

17. C. P. Miller; D. H. Kaufman; Synlett, 2000, 8, 1169-1171.

18. N. Jiang; A. J. Ragauskas; Tetrahedron lett., 2010, 51, 4479-4481.

19. D. Zhang; Y. Huang; E. Zhang; R. Yi; C. Chen; L. Yu; Q. Xu; Adv. Synth. Catal., 2018, 360, 784-790.

20. K. S. Lee; H. S. An; C. Y. Hwang; Bull. Korean. Chem. Soc., 2012, 33, 3173-3174.

21. K. W. Rosenmund; E. Struck; Ber. Dtsch. Chem. Ges., 1919, 2, 1749-1756.

22. S. H. Yang; S. Chang; Org. Lett., 2001, 3, 4209-4211.

23. P. Yan P; P. Batamack; G. S. Prakas; G. A. Olah; Catal. Lett., 2005, 101, 141-143.

24. J. Bird; D. G. M. Diaper; Can. J. Chem., 1969, 47, 145-150.

25. R. M. Denton; J. An; P. Lindovska; W. Lewis; Tetrahedon, 2012, 68, 2899-2905.

26. N. Iranpoor; H. Firouzabadi; G. Aghapour; Synt. Commun., 2002, 32, 2535-2541.

27. Y. Song; D. Shen; Q. Zhang; B. Chen; G. Xu; Tetrahedron Lett.,2014, 55, 639-641.

28. X. C. Wang; L. Li; Z. J. Quan; H. P. Gong; H. L. Ye; X. F. Cao; Chin. Chem. Lett., 2009, 20, 651-655.

29. M. Terhorst; C. Plass; A. Guntermann; T. Jolme; J. Rösler; D. Panke; H. Gröger; D. Vogt; A. J. Vorholt; T. Seidensticker; Green Chem., 2020, 22, 7974-7982.

30. I. Damljanović; M. Vukićević; R. D. Vukićević; Monatsh. Chem., 2006, 137, 301-305.

31. X. Jiang; X. Hu; Y. Lin; Y. Yan; P. Li; R. Bai; Y. Xie; Tetrahedron, 2018, 74, 5879-5885.

32. R. Ding; Y. Liu; M. Han; W. Jiao; J. Li; H. Tian; B. Sun; J. Org. Chem., 2018, 83, 12939-12944.

33. S. M. Masjed; B. Akhlaghinia; M. Zarghani; N. Razavi; Aust. J. Chem. 2016, 70, 33-43.

34. A. Ghorbani-Choghamarani; M. A. Zofigol; M. Hajjami; S. Sardari; Synth. Commun., 2013, 43, 52-58.

35. A. R. Sardarian; Z. Shahsavari-Fard; H. R. Shahsavari; Z. Ebrahimi; Tetrahedron Lett. 2007, 48, 2639-2643.

36. X. Liu; C. Wu; P. Zhou; M. Jia; L. Zhu; Z Zhang; Angew. Chem. Int. Ed., 2025, 64, e202413799.

37. C-H. Yang; J. M. Williams; Org. Lett., 2004, 6, 2837-2840.

38. R. Li; J. Shi; X. Zhou; Z. Li; Y. Zhao; Z. Liu; J. Wang; ACS Sustain. Chem. Eng., 2024, 12, 11338-11346.

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Published

2025-12-16

How to Cite

ULUDAG, N., & SANLİ, A. (2025). A NEW REAGENT FOR SYNTHESIS OF NITRILES FROM ALDOXIMES USING ALUMINIUM (III) TRIFLATE. Studia Universitatis Babeș-Bolyai Chemia, 70(4), 97–106. https://doi.org/10.24193/subbchem.2025.4.06

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