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Vol. 30 No. 3 (2018): Vol 30 Issue 3

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Palladium(II) Acetate as Catalyst in Transvinylation Reactions of Hydroxycinnamic Acid and Its Derivatives

https://doi.org/10.14233/ajchem.2018.21033
L.O. Kadidae
Department of Chemistry Faculty of Mathematics and Natural Sciences, Halu Oleo University, Kendari, Southeast Sulawesi, 93232, Indonesia
A. Usami
Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-Machi, Kanazawa, 920-1192, Japan
M. Honda
Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-Machi, Kanazawa, 920-1192, Japan

Corresponding Author(s) : L.O. Kadidae

lkadidae@gmail.com

Asian Journal of Chemistry, Vol. 30 No. 3 (2018): Vol 30 Issue 3

Abstract

The study on application of palladium(II) acetate as catalyst in transvinylation reactions of hydroxycinnamic acids has been done. This study was intended to assess the capability of palladium(II) acetate as a safer replacement for mercuric(II) catalysts in transvinylation reactions of hydroxycinnamic acids and its derivatives. Optimizing the performance of the catalyst by applying several additional catalysts in the reactions was firstly done. Among those catalysts, KOH and H2SO4 showed significant impacts on the yields of the transvinylation reactions. It increased to 96 % when KOH was added and to 95 % when H2SO4 was added, compared to only 66 % when palladium(II) acetate alone was employed. Adding either KOH or H2SO4 along with the primary catalyst of palladium(II) acetate in transvinylation reactions of hydroxycinnamic acids gave the desired products in good yields. This proved that palladium(II) acetate was capable of catalyzing the transvinylation reactions of hydroxycinnamic acid and its derivatives to produce some vinyl esters.

Keywords

Palladium(II) acetate Catalyst Hydroxycinnamic acid Transvinylation
Kadidae, L., Usami, A., & Honda, M. (2018). Palladium(II) Acetate as Catalyst in Transvinylation Reactions of Hydroxycinnamic Acid and Its Derivatives. Asian Journal of Chemistry, 30(3), 589–593. https://doi.org/10.14233/ajchem.2018.21033
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References
  1. R.J. Fessenden and J.S. Fessenden, Organic Chemistry, Part 2, Translated in Indonesian by A.H. Pudjaatmaka, Penerbit Erlangga, Jakarta, edn 3, pp. 82-84 (1990).
  2. J. McMurry and E. Simanek, Fundamentals of Organic Chemistry, Thomson Higher Education, California, edn 6, pp. 307-308 (2007).
  3. L.O. Kadidae, A. Usami, T. Koyama, M. Honda and K. Kunimoto, Eur. J. Chem., 6, 367 (2015); https://doi.org/10.5155/eurjchem.6.4.367-373.1298.
  4. W.O. Herrmann and W. Haehnel, Process of Preparing Vinyl Esters, US Patent 2245131 (1941).
  5. W.J. Toussaint and G. McDowell Jr., Preparation of Vinyl Esters, US Patent 2299862 (1942).
  6. R.L. Adelman, J. Org. Chem., 14, 1057 (1949); https://doi.org/10.1021/jo01158a015.
  7. J. Kavitha, D. Rajasekhar, G.V. Subbaraju and G.N. Ramesh, Indian J. Chem., 38B, 1280 (1999).
  8. D. Swern and E.F. Jordan Jr., Org. Synth., 30, 106 (1950); https://doi.org/10.15227/orgsyn.030.0106.
  9. Z. Tan and F. Shahidi, Food Chem., 133, 1427 (2012); https://doi.org/10.1016/j.foodchem.2012.02.030.
  10. M. Mastihubová and V. Mastihuba, Bioorg. Med. Chem. Lett., 23, 5389 (2013); https://doi.org/10.1016/j.bmcl.2013.07.051.
  11. C. Gao, P. Mayon, D.A. MacManus and E.N. Vulfson, Biotechnol. Bioeng., 71, 235 (2000); https://doi.org/10.1002/1097-0290(2000)71:3<235::AID-BIT1013> 3.0.CO;2-M.
  12. D. Yang, S. Ding, J. Huang and K. Zhao, Chem. Commun., 49, 1211 (2013); https://doi.org/10.1039/c2cc37779a.
  13. P.A. Caruana and A.J. Frontier, Tetrahedron, 63, 10646 (2007); https://doi.org/10.1016/j.tet.2007.08.008.
  14. http://sdbs.db.aist.go.jp/sdbs/cgi-bin/direct_frame_top.cgi.
  15. P.J. Kocienski, Protecting Groups, Stuttgart, edn 3, pp. 115-116 (2005).
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