4.6 Article

Formal [4+2] Reaction between 1,3-Diynes and Pyrroles: Gold(I)-Catalyzed Indole Synthesis by Double Hydroarylation

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 4, Pages 1463-1467

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201405903

Keywords

carbazoles; cascade reaction; gold catalysis; hydroarylation; indoles

Funding

  1. Ministry of Education, Culture, Sports, Science and Technology, Japan
  2. Japan Society for the Promotion of Science for Young Scientists
  3. Grants-in-Aid for Scientific Research [23390025, 24689001] Funding Source: KAKEN

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Indole synthesis by a gold(I)-catalyzed intermolecular formal [4+2] reaction between 1,3-diynes and pyrroles has been developed. This reaction involves the hydroarylation of 1,3-diynes with pyrroles followed by an intramolecular hydroarylation to give the 4,7-disubstituted indoles. This reaction can also be applied to the synthesis of carbazoles when indoles are used as the nucleophiles instead of pyrroles.

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