Synthesis of 2-Iodoazulenes by the Iododeboronation of Azulen-2-ylboronic Acid Pinacol Esters with Copper(I) Iodide

Masahiro Narita, Toshihiro Murafuji, Saki Yamashita, Masayuki Fujinaga, Kumiko Hiyama, Yurie Oka, Fumito Tani, Shin Kamijo, Katsuya Ishiguro

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16 Citations (Scopus)

Abstract

Azulen-2-ylboronic acid pinacol ester, prepared by iridium-catalyzed C-H borylation of azulene, efficiently underwent iododeboronation with a stoichiometric amount of copper(I) iodide. This reaction allowed the synthesis of 2-iodoazulene in only two steps starting from azulene. This methodology was successfully applied to analogous azulenes.

Original languageEnglish
Pages (from-to)1298-1303
Number of pages6
JournalJournal of Organic Chemistry
Volume83
Issue number3
DOIs
Publication statusPublished - Feb 2 2018

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Narita, M., Murafuji, T., Yamashita, S., Fujinaga, M., Hiyama, K., Oka, Y., Tani, F., Kamijo, S., & Ishiguro, K. (2018). Synthesis of 2-Iodoazulenes by the Iododeboronation of Azulen-2-ylboronic Acid Pinacol Esters with Copper(I) Iodide. Journal of Organic Chemistry, 83(3), 1298-1303. https://doi.org/10.1021/acs.joc.7b02820