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

Research output: Contribution to journalArticle

7 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

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Azulenes
Esters
Iridium
Acids
azulene
cuprous iodide

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Narita, M., Murafuji, T., Yamashita, S., Fujinaga, M., Hiyama, K., Oka, Y., ... 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

Synthesis of 2-Iodoazulenes by the Iododeboronation of Azulen-2-ylboronic Acid Pinacol Esters with Copper(I) Iodide. / Narita, Masahiro; Murafuji, Toshihiro; Yamashita, Saki; Fujinaga, Masayuki; Hiyama, Kumiko; Oka, Yurie; Tani, Fumito; Kamijo, Shin; Ishiguro, Katsuya.

In: Journal of Organic Chemistry, Vol. 83, No. 3, 02.02.2018, p. 1298-1303.

Research output: Contribution to journalArticle

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, vol. 83, no. 3, pp. 1298-1303. https://doi.org/10.1021/acs.joc.7b02820
Narita, Masahiro ; Murafuji, Toshihiro ; Yamashita, Saki ; Fujinaga, Masayuki ; Hiyama, Kumiko ; Oka, Yurie ; Tani, Fumito ; Kamijo, Shin ; Ishiguro, Katsuya. / Synthesis of 2-Iodoazulenes by the Iododeboronation of Azulen-2-ylboronic Acid Pinacol Esters with Copper(I) Iodide. In: Journal of Organic Chemistry. 2018 ; Vol. 83, No. 3. pp. 1298-1303.
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