1,3-Iodo-amination of 2-methyl indoles via Csp2–Csp3 dual functionalization with iodine reagent

Katsuhiko Moriyama; Tsukasa Hamada; Kazuma Ishida; Hideo Togo

doi:10.1039/C8CC00352A

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1,3-Iodo-amination of 2-methyl indoles via C_sp²–C_sp³ dual functionalization with iodine reagent†

Katsuhiko Moriyama,

*^ab Tsukasa Hamada,^a Kazuma Ishida^a and Hideo Togo

Author affiliations

* Corresponding authors

^a Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan
E-mail: moriyama@faculty.chiba-u.jp

^b Molecular Chirality Research Center, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

A 1,3-iodo-amination with iodine reagent that involved the C_sp²–C_sp³ dual functionalization of 2-methyl indoles was developed to provide 2-aminomethyl-3-iodo-indole derivatives. The iodo-amination proceeded via a 1,4-transfer of an imide group through the formation of an indolyl(phenyl)iodonium imide using PhI(OAc)₂, followed by an iodination using DIH or a double iodination of indole using excess DIH.

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Article information

DOI: https://doi.org/10.1039/C8CC00352A
Article type: Communication
Submitted: 15 Jan 2018
Accepted: 09 Feb 2018
First published: 09 Feb 2018

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Chem. Commun., 2018,54, 4258-4261

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1,3-Iodo-amination of 2-methyl indoles via C_sp²–C_sp³ dual functionalization with iodine reagent

K. Moriyama, T. Hamada, K. Ishida and H. Togo, Chem. Commun., 2018, 54, 4258 DOI: 10.1039/C8CC00352A

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