A Simple and Efficient Acylation Reaction Over Zinc Triflate as a New Catalyst

Abstract

The amide containing structure is found chemistry and related science. As a consequence, methods for the N-acylation of amines occupies a large place in organic chemistry. In this study, Zinc triflate acylation between aniline derivatives and furan-2-carbonyl chloride was investigated under mild conditions. Also, different types of amides was obtained in very good yields at room temperature and purity after a simple workup. This newly developed method is presented as a new method in organic synthesis.

Keywords

• Zinc triflate
• Heterocyclic compound
• Aniline derivatives.

References

1. Alleti R, Oh W. S, Perambuduru M, Afrasiabi Z, Sinn E, Reddy V. P. (2005). Gadolinium triflate immobilized in imidazolium based ionic liquids: A recyclable catalyst and green solvent for acetylation of alcohols and amines. Green Chemistry, 77 (7), 203-206. Doi: 10.1039/B416359A
2. Bejblova M, Prochazkova D, Cejka J. (2009). Acylation reactions over zeolites and mesoporous catalysts. ChemSusChem, 2 (6), 486-499. Doi: 10.1002/cssc.200900007.
3. Cheung C. W, Shen Ni, Wang S.-P, Ullah A, Hu X, Ma J.-A. (2013). Manganese-mediated reductive amidation of esters with nitroarenes. Journal Name, 6(6), 757-761. Doi: 10.1039/c8qo01405a
4. Devendar P, Qu R.-Y, Kang W.-Ming, He B, Yang G.-Y. (2018). Palladium-catalyzed cross-coupling Rractions: A powerful tool for the synthesis of agrochemicals. Journal of Agricultural and Food Chemistry, 66 (34), 8914-8934. Doi: 10.1021/acs.jafc.8b03792
5. Kobayashi K, Ahmed M S. M, Mori A. (2006) Introduction of ethynylene and thienylene spacers into 2,5-diarylthiazole and 2,5-diarylthiophene. Tetrahedron, 62 (41), 9548-9553. Doi: 10.1016/j.tet.2006.07.097
6. Masui K, Mori A, Okano, Takamura K, Kinoshita M, Ikeda T. (2004). Syntheses and properties of donor-acceptor-type 2,5-diarylthiophene and 2,5-diarylthiazole. Organic Letters, 6 (12), 2011-2014. doi: 10.1021/ol049386z
7. Moreno-Fuquen, R, Azca´rate,a A, Kennedy A. R, Gilmourb D, De Almeida Santos R. H. (2013). N- (2-Nitrophenyl)furan-2-carbozamide. Acta Crystallographica Section E, E70, o613. Doi: 10.1107/S160053681400912X
8. Nakae Y, Kusaki I, Sato T. (2001). Lithium perchlorate catalyzed acetylation of alcohols under mild reaction conditions. Synlett, 10, 1584-1586. Doi: 10.1055/s-2001-17483

9. Nicolauo K. C, Baulger P. G, Sarlah D. (2005). Palladium-catalyzed cross-coupling reactions in total synthesis. Angewandte Chemie International Edition, 44 (29), 4442-89. Doi: 10.1002/anie.200500368
10. Orita A, Tanahashi C, Kakuda A, J. (2001). Highly powerful and practical acylation of alcohols with acid anhydride catalyzed by Bi(OTf)3. Journal of Organic Chemistry, 66 (26), 8926-8934. Doi: 10.1021/jo0107453
11. Roncalı J. (1992), Conjugated poly(thiophenes): synthesis, functionalization, and applications. Chemical Reviews, 92 (4), 711-738. Doi: 10.1021/cr00012a009
12. Sarvari M. H, Shargi H. (2004). Reactions on a solid surface. A simple economical and efficient Friedel-Crafts acylation reaction over zinc oxide (ZnO) as a new catalyst. Journal of Organic Chemistry, 69 (20), 6953-6956. Doi: 10.1021/jo0494477
13. Scmidt N. G, Pavkov-Keller T, Richter N, Wiltschi B, Gruber K, Kroutil W. (2017). Biocatalytic Friedel–Crafts acylation and Fries Reaction. Angewandte Chemie International Edition, 56 (26), 7615-7619. Doi: 10.1002/anie.201703270
14. Surya K. D. (2004). Ruthenium(III) chloride catalyzed acylation of alcohols, phenols, thiols, and amines. Tetrahedron Letters, 45 (14), 2919-2922. Doi: 10.1016/j.tetlet.2004.02.071
15. Wu Y, Guo L, Liu Y, Xiang J, Jiang J. (2021) Fe-mediated synthesis of N-aryl amides from nitroarenes and acyl chlorides. Royal Society Chemistry Advances, 11, 15290-15295. Doi: 10.1039/D0RA10868E
16. Yogesh Kumar K, Pradeep Kumar C. B, Prased K. N. N, Jeon B.-H, Alsalme A. Prashanth M. K. (2022). Microwave-assisted N-alkylation of amines with alchols catalyzed by MnCl2: Anticancer, docking, and DFT Studies. Archiv Der Pharmazie, e2100443. Doi: 10.1002/ardp.202100443
17. Zhang G, Wen X, Wang Y, Mo W, Ding, C. (2012). Recent advances in oxidative deoximation. Progress in Chemistry, 24, 361-369.