Transition-Metal-Free Synthesis of Carbazoles and Indoles by an SN Ar-Based "Aromatic Metamorphosis" of Thiaarenes.

• Bhanuchandra, M

• Murakami, Kei

• Vasu, Dhananjayan

• Yorimitsu, Hideki

• Osuka, Atsuhiro

Abstract

Dibenzothiophene dioxides, which are readily prepared through oxidation of the parent dibenzothiophenes, undergo nucleophilic aromatic substitution with anilines intermolecularly and then intramolecularly to yield the corresponding carbazoles in a single operation. The "aromatic metamorphosis" of dibenzothiophenes into carbazoles does not require any heavy metals. This strategy is also applicable to the synthesis of indoles. Since electron-deficient thiaarene dioxides exhibit interesting reactivity, which is not observed for that the corresponding electron-rich azaarenes, a combination of a thiaarene-dioxide-specific reaction with the SN Ar-based aromatic metamorphosis allows transition-metal-free construction of difficult-to-prepare carbazoles.

Journal

• Angewandte Chemie - International Edition

  Angewandte Chemie - International Edition 54 (35), 10234-10238, 2015-07-15

  wiley

Keywords

• amination
• aromatic substitution
• fluorescence
• sulfur heterocycles
• synthetic methods

Details

• CRID: 1050282810795467776
• NII Article ID: 120005674604
• NII Book ID: AA0052535X
• ISSN: 14337851
• HANDLE: 2433/201996
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • CiNii Articles