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 › peer-review

45 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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title = "Synthesis of 2-Iodoazulenes by the Iododeboronation of Azulen-2-ylboronic Acid Pinacol Esters with Copper(I) Iodide",

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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doi = "10.1021/acs.joc.7b02820",

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T1 - Synthesis of 2-Iodoazulenes by the Iododeboronation of Azulen-2-ylboronic Acid Pinacol Esters with Copper(I) Iodide

AU - Narita, Masahiro

AU - Murafuji, Toshihiro

AU - Yamashita, Saki

AU - Fujinaga, Masayuki

AU - Hiyama, Kumiko

AU - Oka, Yurie

AU - Tani, Fumito

AU - Kamijo, Shin

AU - Ishiguro, Katsuya

PY - 2018/2/2

Y1 - 2018/2/2

N2 - 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.

AB - 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.

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ER -

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

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