4.4 Article

Synthesis of 3-Allenylindoles and 3-Dienylindoles by Bronsted Acid Catalyzed Allenylation of 2-Arylindoles with Tertiary Propargylic Alcohols

Journal

SYNLETT
Volume -, Issue 12, Pages 1985-1989

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0029-1217543

Keywords

catalysis; indoles; allenes; dienes; nucleophilic substitution

Funding

  1. Junta de Castilla y Leon [BU012A06]
  2. Ministerio de Educacion y Ciencia (MEC)
  3. FEDER [CTQ2007-61436/BQU]
  4. Young Foreign Researchers [SB2006-0215]

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The Bronsted acid catalyzed direct nucleophilic substitution of tertiary propargylic alcohols with 2-aryl-substituted indoles has been studied. A competitive allenylation process takes place with appropriate substituents on the alkynol moiety. Starting from 2-arylindoles, new 3-allenyl and 3-dienylindole derivatives have been easily synthesized.

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