Efficient Synthesis of Diacetoxyiodoarenes via Intramolecular Rearrangement

Page: [911 - 914] Pages: 4

  • * (Excluding Mailing and Handling)

Abstract

This study introduces a concise and efficient method for preparing diacetoxyiodoarenes from the corresponding iodoarenes. In the presence of acetic anhydride, iodoarenes were oxidized to diacetoxyiodoarenes by sodium perborate in acetic acid under argon protection at 55°C in ideal yields. Through this method, 10 diacetoxyiodoarenes were obtained smoothly.

Keywords: Diacetoxyiodoarenes, acetic anhydride, sodium perborate, intramolecular rearrangement, ideal yields, iodoarenes.

Graphical Abstract

[1]
Okamoto, N.; Miwa, Y.; Minami, H.; Takeda, K.; Yanada, R. Angew. Chem. Int. Ed., 2009, 48, 9693.
[2]
Kalesse, M.; Lansberg, D. Synlett, 2010, 1104.
[3]
Khatri, H.R.; Zhu, J. Chem. Eur. J., 2012, 18, 12232.
[4]
Jia, Z.; Galvez, E.; Sebastian, R.M.; Pleixats, R.; Alvarez-Larena, A.; Martin, E.; Vallribera, A.; Shafir, A. Angew. Chem. Int. Ed., 2014, 53, 11298.
[5]
Willgerodt, C. Ber. Dtsch. Chem. Ges., 1892, 25, 3494.
[6]
Kitamura, T.; Fujiwara, Y. Org. Prep. Proced. Int., 1997, 29, 409.
[7]
Hossain, M.D.; Kitamura, T. J. Org. Chem., 2005, 70, 6984.
[8]
Yamada, Y.; Kashima, K.; Okawara, M.J. Polym. Sci. Polym. Lett., 1976, 14, 65-71.
[9]
McKillop, A.; Kemp, D. Tetrahedron, 1989, 45, 3299-3306.
[10]
Leffler, J.E.; Story, L.J. J. Am. Chem. Soc., 1967, 89, 2333-2338.
[11]
Dixon, L.I.; Carroll, M.A.; Gregson, T.J.; Ellames, G.J.; Harrington, R.W.; Clegg, W. Eur. J. Org. Chem., 2013, 2334-2345.
[12]
Kazmierczak, P.; Skulski, L.; Kraszkiewicz, L. Molecules, 2001, 6, 881-891.