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

J Org Chem. 2018 Feb 2;83(3):1298-1303. doi: 10.1021/acs.joc.7b02820. Epub 2018 Jan 19.

Authors

Masahiro Narita¹, Toshihiro Murafuji^{1

2

3}, Saki Yamashita², Masayuki Fujinaga³, Kumiko Hiyama³, Yurie Oka³, Fumito Tani⁴, Shin Kamijo^{1

2}, Katsuya Ishiguro^{1

2}

Affiliations

¹ Graduate School of Sciences and Technology for Innovation, Yamaguchi University , Yamaguchi 753-8512, Japan.
² Department of Chemistry, Faculty of Science, Yamaguchi University , Yamaguchi 753-8512, Japan.
³ Graduate School of Medicine, Yamaguchi University , Yamaguchi 753-8512, Japan.
⁴ Institute for Materials Chemistry and Engineering, Kyushu University , Fukuoka 819-0395, Japan.

PMID: 29300095
DOI: 10.1021/acs.joc.7b02820

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.

Publication types

Research Support, Non-U.S. Gov't