4.7 Article

Gold-Catalyzed Intramolecular Alkyne Cycloisomerization Cascade: Direct Synthesis of Aryl-Annulated[a]carbazoles from Aniline-Substituted Diethynylarenes

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 352, Issue 2-3, Pages 368-372

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900880

Keywords

alkynes; carbazoles; cascade reactions; gold catalysis; heterocycle synthesis

Funding

  1. Kaken Pharmaceutical Co., Ltd
  2. Ministry of Education, Culture, Sports, Science and Technology of Japan
  3. Japan Society for the Promotion of Science (JSPS)
  4. Grants-in-Aid for Scientific Research [22590005] Funding Source: KAKEN

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Aniline-substituted diethynylarenes, which are readily synthesized through Sonogashira coupling reactions from commercially available 1,2-dihaloarenes, directly produce aryl- and heteroaryl-annulated[a]carbazoles by the gold-catalyzed intramolecular cascade hydroamination/cycloisomerization without producing theoretical by-products. This new atom-economical route is easily applicable to various aryl-annulated[a]carbazoles containing an alkyl, aryl or ester substituent.

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