Synthesis of 2-Iodoazulenes by the Iododeboronation of Azulen-2-ylboronic Acid Pinacol Esters with Copper(I) Iodide
M. Narita, T. Murafuji, S. Yamashita, M. Fujinaga, K. Hiyama, Y. Oka, F. Tani, S. Kamijo, K. Ishiguro
J. Org. Chem., 2018, 83, 1298–1303
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.