Cu(I)-catalyzed intramolecular cyclization of ene-carbamates: synthesis of indoles and pyrrolo[2,3- c]pyridines

Over the past few years, the use of palladium-catalyzed aromatic carbon–nitrogen bond forming reactions by the cross-coupling of aryl halides or triflates and amines has become a useful synthetic tool. Herein, we describe a copper(I) catalyst system that allows efficient synthesis of functionalized...

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Bibliographic Details
Published in:Tetrahedron letters 2005-12, Vol.46 (51), p.8877-8880
Main Authors: Barberis, Claude, Gordon, Thomas D., Thomas, Christine, Zhang, Xiaolei, Cusack, Kevin P.
Format: Article
Language:English
Subjects:
Copper catalysis
Indole
l-Proline
Pyrrolo[2,3- c]pyridine
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Summary:Over the past few years, the use of palladium-catalyzed aromatic carbon–nitrogen bond forming reactions by the cross-coupling of aryl halides or triflates and amines has become a useful synthetic tool. Herein, we describe a copper(I) catalyst system that allows efficient synthesis of functionalized indoles and pyrrolo[2,3- c]pyridines. This method takes advantage of amino acid promoted copper coupling of amines with aryl halides, in particular, the use of the CuI/ l-proline catalyst system.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.10.077