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UV-Promoted Metal- and Photocatalyst-Free Direct Conversion of Aromatic Aldehydes to Nitriles

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Abstract

An efficient, simple, and catalyst-free UV-induced functional group transformation of aromatic aldehydes to nitriles has been reported. The developed strategy delivers various functionalized aromatic nitriles with high yields and purity. The UV irradiation activates the carbonyl group of aldehydes and leads to the formation of aldoxime intermediate, further resulting in the generation of nitriles. The striking highlights of the reported methodology are simple reaction conditions, good yields, UV-promoted transformation, and catalyst-free synthesis. Due to the above-mentioned advantages, the methodology provides a whip hand toward environmentally friendly chemical synthesis.

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REFERENCES

  1. Fleming, F.F., Yao, L., Ravikumar, P.C., Funk, L., Shook, B.C., J. Med. Chem., 2010, vol. 53, p. 7902. https://doi.org/10.1021/jm100762r

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Fleming, F.F., Nat. Prod. Rep., 1999, vol. 16, p. 597. https://doi.org/10.1039/A804370A

    Article  CAS  Google Scholar 

  3. Schmiedl, R., Bottner, R., Zacharias, H., Meier, U., and Welge, K.H., Opt. Commun., 1979, vol. 29, p. 329. https://doi.org/10.1016/0030-4018(79)90208-6

    Article  Google Scholar 

  4. Garber, A.J., Foley, J.E., Banerji, M.A., Ebeling, P., Gudbjörnsdottir, S., Camisasca, R.P., Couturier, A., Baron, and M.A., Diabetes, Obes. Metab., 2008, vol. 10, p. 1047. https://doi.org/10.1111/j.1463-1326.2008.00859.x

    Article  CAS  Google Scholar 

  5. Recanatini, M., Bisi, A., Cavalli, A., Belluti, F., Gobbi, S., Rampa, A., Valenti, P., Palzer, M., Palusczak, A., and Hartmann, R.W., J. Med. Chem., 2001, vol. 44, p. 672. https://doi.org/10.1021/jm000955s

    Article  CAS  PubMed  Google Scholar 

  6. Bayram, M., De Luca, L., Massie, M.B., and Gheorghi­ade, M., Am. J. Cardiol., 2005, vol. 96, p. 47. https://doi.org/10.1016/j.amjcard.2005.07.021

    Article  CAS  Google Scholar 

  7. Kwak, E.L., Sordella, R., Bell, D.W., GodinHeymann, N., Okimoto, R.A., Brannigan, B.W., Harris, P.L., Driscoll, D.R., Fidias, P., and Lynch, T.J., Proc. Natl. Acad. Sci. U. S. A., 2005, vol. 102, p. 7665. https://doi.org/10.1073/pnas.0502860102

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Hughes, C.A., Robinson, L., Tseng, A., and Mac­Arthur, R.D., Expert Opin. Pharmacother., 2009, vol. 10, p. 2445. https://doi.org/10.1517/14656560903176446

    Article  CAS  PubMed  Google Scholar 

  9. Liangzhen, C., Xin, L., Tao, X., and Shen, D., Synth. Commun., 2004, vol. 34, p. 1215. https://doi.org/10.1081/SCC-120030308

    Article  CAS  Google Scholar 

  10. Friedman, L. and Shechter, H., J. Org. Chem., 1960, vol. 25, p. 877. https://doi.org/10.1021/jo01076a001

    Article  CAS  Google Scholar 

  11. Bose, D.S. and Jayalakshmi, B., J. Org. Chem., 1999, vol. 64, p. 1713. https://doi.org/10.1021/jo981839o

    Article  CAS  PubMed  Google Scholar 

  12. Yang, S.H. and Chang, S., Org. Lett., 2001, vol. 3, p. 4209. https://doi.org/10.1021/ol0168768

    Article  CAS  PubMed  Google Scholar 

  13. Jin, M., Mun, J., and Kim, J., Tetrahedron Lett., 2017, vol. 58, p. 4695. https://doi.org/10.1016/j.tetlet.2017.11.002

    Article  CAS  Google Scholar 

  14. Mitra, B., Pariyar, G.C., Singha, R., and Ghosh, P., Tetrahedron Lett., 2017, vol. 58, p. 2298. https://doi.org/10.1016/j.tetlet.2017.04.100

    Article  CAS  Google Scholar 

  15. Ding, R., Liu, Y., Han, M., Jiao, W., Li, J., Tian, H., and Sun, B., J. Org. Chem., 2018, vol. 83, p. 12939. https://doi.org/10.1021/acs.joc.8b02190

    Article  CAS  PubMed  Google Scholar 

  16. Hyodo, K., Togashi, K., Oishi, N., Hasegawa, G., and Uchida, K., Org. Lett., 2017, vol. 19, p. 3005. https://doi.org/10.1021/acs.orglett.7b01263

    Article  CAS  PubMed  Google Scholar 

  17. Fang, C., Li, M., Hu, X., Mo, W., Hu, B., Sun, N., Jin, L., and Shen, Z., Adv. Synth. Catal., 2016, vol. 358, p. 1157. https://doi.org/10.1002/adsc.201501130

    Article  CAS  Google Scholar 

  18. Ghosh, P., Saha, B., Pariyar, G.C., Tamang, A., and Subba, R., Tetrahedron Lett., 2016, vol. 57, p. 3618. https://doi.org/10.1016/j.tetlet.2016.06.125

    Article  CAS  Google Scholar 

  19. Verma, F., Shukla, P., Bhardiya, S.R., Singh, M., Rai, A., and Rai, V.K., Catal. Commun., 2019, vol. 119, p. 76. https://doi.org/10.1016/j.catcom.2018.10.031

    Article  CAS  Google Scholar 

  20. Liu, Q. and Wu, L.-Z., Natl. Sci. Rev., 2017, vol. 4, p. 359. https://doi.org/10.1093/nsr/nwx039

    Article  CAS  Google Scholar 

  21. Fukui, K., Yonezawa, T., Nagata, C., and Shingu, H., J. Chem. Phys., 1954, vol. 2, p. 1433. https://doi.org/10.1063/1.1740412

    Article  Google Scholar 

  22. Manolopoulos, D.E., May, J.C., and Down, S.E., Chem. Phys. Lett., 1991, vol. 181, p. 105. https://doi.org/10.1016/0009-2614(91)90340-F

    Article  CAS  Google Scholar 

  23. Sampath Kumar, H.M., Subba Reddy, B.V., Tirupathi Reddy, P., and Yadav, J.S., Synthesis, 1999, vol. 4, p. 586. https://doi.org/10.1055/s-1999-3450

    Article  Google Scholar 

  24. Khezri, S.H., Azimi, N., Mohammedvali, M., and Eftekharisis, B., Arkivoc, 2007, vol. 2007, part (xv), p. 162. https://doi.org/10.3998/ark.5550190.0008.f16

    Article  Google Scholar 

  25. Venkat Narsaiah, A. and Nagaiah, K., Adv. Synth. Catal., 2004, vol. 346, p. 1271. https://doi.org/10.1002/adsc.200404059

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

The authors thank the CHRIST (Deemed to be University) for the research project funding (MRP no. MRPDSC-1722) and providing the facilities to carry out this research.

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Authors and Affiliations

  1. Department of Chemistry, CHRIST (Deemed to be University), 560029, Bengaluru, India

    F. Joy, F. Peter, P. C. Gokul & A. Nizam

  2. Department of Chemistry, B.M.S. College of Engineering, 560019, Bengaluru, India

    S. Chinnam

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  1. F. Joy
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  2. F. Peter
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  3. P. C. Gokul
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Correspondence to A. Nizam.

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Joy, F., Peter, F., Gokul, P.C. et al. UV-Promoted Metal- and Photocatalyst-Free Direct Conversion of Aromatic Aldehydes to Nitriles. Russ J Org Chem 58, 379–384 (2022). https://doi.org/10.1134/S1070428022030174

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