Formation of homoallylic bromohydrins in indium-mediated allylation reactions of phenacyl bromides in aqueous solution

Mei Huey Lin, Chung Kai Kuo, Wei Cheng Lin, Yen Chih Huang, Yu Ting Tsai, Kung Yu Liang, Yi Syuan Li, Tsung Hsun Chuang

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Abstract

A method is described for carrying out indium-mediated allylation reactions of phenacyl bromides in aqueous solution that form homoallylic bromohydrins. By employing subsequent base treatment, the homoallylic bromohydrins were converted to allylic epoxides. Finally, the process has been used as a key step in a concise sequence for the synthesis of 3-allylbenzofuran.

Original languageEnglish
Pages (from-to)8263-8268
Number of pages6
JournalTetrahedron
Volume69
Issue number38
DOIs
Publication statusPublished - 2013 Sep 23

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Lin, M. H., Kuo, C. K., Lin, W. C., Huang, Y. C., Tsai, Y. T., Liang, K. Y., Li, Y. S., & Chuang, T. H. (2013). Formation of homoallylic bromohydrins in indium-mediated allylation reactions of phenacyl bromides in aqueous solution. Tetrahedron, 69(38), 8263-8268. https://doi.org/10.1016/j.tet.2013.07.012