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Short Paper | Regular issue | Vol 91, No. 6, 2015, pp.1244-1255
Published online, 11th May, 2015
DOI: 10.3987/COM-15-13213
Synthesis of 3-Ethenylindoles via Intramolecular Cyclization of Aryl Radical with Allene Generated by Samarium(II) Diiodide

Kenji Suzuki, Hiroki Iwasaki, Fumihito Ichiyoshi, Mao Tominaga, Naoto Kojima, Minoru Ozeki, and Masayuki Yamashita*

*Kyoto Pharmaceutical University, 5 Misasagi-Nakauchi, Yamashina, Kyoto, Japan

Abstract

N-(2,3-Butadien-1-yl)-N-(tert-butoxycarbonyl)-2-iodoanilines cyclized intramolecularly to form 3-ethenyl-2,3-dihydroindoles after treatment with samarium(II) diiodide. The dihydroindoles were easily oxidized to the corresponding 3-ethenylindoles in good to moderate yields.