General and Efficient Indole Syntheses Based on Catalytic Amination Reactions
- 7 January 2005
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (3), 439-442
- https://doi.org/10.1021/ol047649j
Abstract
Highly flexible and efficient syntheses of the indole backbone are presented starting from o-alkynylhaloarenes. These transformations proceed via a palladium- or a copper-catalyzed amination reaction and a subsequent cyclization reaction in good to excellent yields. Furthermore, a multicatalytic one-pot indole synthesis starting from o-chloroiodobenzene is viable using a single catalyst consisting of an N-heterocyclic carbene palladium complex and CuI.Keywords
This publication has 7 references indexed in Scilit:
- A Flexible, Palladium‐Catalyzed Indole and Azaindole Synthesis by Direct Annulation of Chloroanilines and Chloroaminopyridines with KetonesAngewandte Chemie International Edition, 2004
- Aqueous Catalytic Pauson–Khand‐Type Reactions of Enynes with Formaldehyde: Transfer Carbonylation Involving an Aqueous Decarbonylation and a Micellar CarbonylationAngewandte Chemie International Edition, 2003
- Copper-catalyzed amination of aryl halides: single-step synthesis of triarylaminesTetrahedron Letters, 2002
- Synthesis of 2,3-Dihydroindoles, Indoles, and Anilines by Transition Metal-Free Amination of Aryl ChloridesThe Journal of Organic Chemistry, 2001
- Versatile Indole Synthesis by a 5-endo-dig Cyclization Mediated by Potassium or Cesium BasesAngewandte Chemie International Edition, 2000
- Heterocyclic ChemistryPublished by Springer Nature ,1995
- Palladium-catalysed cyclization of 2-alkynylanilines to 2-substituted indoles under an acidic two-phase systemJournal of Organometallic Chemistry, 1994