Cis -3-Azido-2-methoxyindolines as safe and stable precursors to overcome the instability of fleeting 3-azidoindoles

Toshiki Yamashiro, Takumi Abe, Masaru Tanioka, Shinichiro Kamino, Daisuke Sawada

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Use of 3-azidoindoles in organic synthesis remains a difficult task owing to their instabilities. Herein, we report a general and concise approach for tackling this problem by using 3-azidoindole surrogates. The surrogates are bench-stable, presumably due to the observed intramolecular O-Nβ bonding. The resultant fleeting intermediates undergo capturing in situ to afford 3-substitued indoles through formal ipso-substitution of the azide group by nucleophiles. In these investigations, we found that the fleeting 3-azidoindoles show a C3-electrophilic character for the first time. This journal is

Original languageEnglish
Pages (from-to)13381-13384
Number of pages4
JournalChemical Communications
Volume57
Issue number98
DOIs
Publication statusPublished - Dec 21 2021

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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