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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

J Org Chem. 2018 Feb 2;83(3):1298-1303.

PMID: 29300095

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP219488990 3-Methyl-2-buten-2-ylboronic acid pinacol ester 3-Methyl-2-buten-2-ylboronic acid pinacol ester 219488-99-0 Price
LS793417 1-methyl-pyrrol-3-ylboronic acid pinacol ester 1-methyl-pyrrol-3-ylboronic acid pinacol ester Price
LS793443 3,5-Difluoro-2-methoxyphenylboronic acid, pinacol ester 3,5-Difluoro-2-methoxyphenylboronic acid, pinacol ester Price
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