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Paper | Regular issue | Vol 89, No. 9, 2014, pp.2105-2121
Published online, 28th August, 2014
DOI: 10.3987/COM-14-13065
Hypervalent Iodine Mediated One-Pot C-H Functionalization at 2α- or 3α-Position of Indole Derivatives

Kazuhiro Higuchi,* Masato Inaba, Asuka Naganuma, Takako Ishizaki, Masanori Tayu, and Tomomi Kawasaki*

*Department of Pharmaceutical Sciences, Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

Abstract

The one-pot 2α- and 3α-functionalization of 2,3-disubstituted indoles using a hypervalent iodine reagent has been developed. The substitution at the 2α-position of indoles took place using phenyliodinebis(trifluoroacetate) with oxygen and carbon nucleophiles in moderate yields. The combination of iodosobenzene and trimethylsilyl azide afforded 3α-azide derivatives preferentially. The latter reaction was applied to other 2,3-disubstituted indoles.