Application of Ynamides in the Synthesis of 2-Amidoindoles

A Pd-catalyzed, one-pot, two-step synthesis of 2-amidoindoles from ynamides and o-iodoanilines is reported. A key highlight of this sequence is that after the Sonogashira reaction, intramolecular cyclization to the indole occurs spontaneously without activation of the alkyne.

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Bibliographic Details
Published in:Organic letters 2009-01, Vol.11 (1), p.221-224
Main Authors: Dooleweerdt, Karin, Ruhland, Thomas, Skrydstrup, Troels
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Amides - chemistry
Aniline Compounds - chemistry
Catalysis
Indoles - chemical synthesis
Indoles - chemistry
Ligands
Molecular Structure
Palladium - chemistry
Stereoisomerism
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Description
Summary:A Pd-catalyzed, one-pot, two-step synthesis of 2-amidoindoles from ynamides and o-iodoanilines is reported. A key highlight of this sequence is that after the Sonogashira reaction, intramolecular cyclization to the indole occurs spontaneously without activation of the alkyne.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol802477d