Synthesis of 2-Substituted Indoles via Migration Reaction of 3-Substituted Indoles with Triflic Acid

Kosuke Nakashima; Yuka Kudo; Yasuyuki Matsushima; Shin-ichi Hirashima; Tsuyoshi Miura

doi:10.1248/cpb.c23-00792

Note

Synthesis of 2-Substituted Indoles via Migration Reaction of 3-Substituted Indoles with Triflic Acid

Kosuke Nakashima , Yuka Kudo, Yasuyuki Matsushima, Shin-ichi Hirashima, Tsuyoshi Miura

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Keywords: indole, migration, 2-substituted indole, trifluoromethanesulfonic acid

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2024 Volume 72 Issue 3 Pages 336-339

DOI https://doi.org/10.1248/cpb.c23-00792

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Abstract

This study showcases the 1,2-migration reactions of alkyl and aryl groups on the indole molecule. Trifluoromethanesulfonic acid effectively facilitates the migration of the substituent from C3- to C2-position of the indole structure. The resulting C2-substituted indoles offer a valuable pathway for the synthesis of natural products and medicinal compounds.

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