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

doi:10.1021/acs.joc.7b02820

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

Department of Applied Molecular Chemistry

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	1298-1303
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	83
Issue number	3
DOIs	https://doi.org/10.1021/acs.joc.7b02820
Publication status	Published - Feb 2 2018

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/acs.joc.7b02820

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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

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 journal › Article

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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.",

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

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AU - Fujinaga, Masayuki

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