Modular synthesis of heptaarylindole

Shin Suzuki, Takashi Asako, Kenichiro Itami, Junichiro Yamaguchi

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The first synthesis of heptaarylindole (HAI) has been accomplished using a coupling/ring transformation strategy. Four readily prepared modular units (diarylthiophenes, 2-arylaziridines, arylboronic acids, and arylalkynes) were joined together to provide key ynamide intermediates. Subsequent inverse electron-demand intramolecular [4 + 2] cycloaddition furnished pentaarylindoles (PAIs) regioselectively. This strategy was also applied to the synthesis of tetraarylazaindole with four different aryl substituents. PAIs underwent further arylations at the C2- and N1-positions, providing HAI with seven different aryl substituents with virtually complete regioselectivity.

Original languageEnglish
Pages (from-to)3771-3776
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number20
DOIs
Publication statusPublished - 2018 Jan 1

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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