Synthesis of Carbazoles by Copper-Catalyzed Intramolecular C–H/N–H Coupling

Synthesis of Carbazoles by Copper-Catalyzed Intramolecular C–H/N–H Coupling

A Cu-catalyzed intramolecular C–H amination for the synthesis of carbazoles has been developed. The key to success is the installation of the picolinamide-based directing group, which is spontaneously removed after the coupling event. The Cu catalysis proceeded smoothly under Pd- and I(III)-free con...

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Veröffentlicht in:Organic letters 2014-06, Vol.16 (11), p.2892-2895
Hauptverfasser: Takamatsu, Kazutaka, Hirano, Koji, Satoh, Tetsuya, Miura, Masahiro
Format: Artikel
Sprache:eng
Schlagworte:
Amides - chemistry
Amination
Carbazoles - chemical synthesis
Carbazoles - chemistry
Copper - chemistry
Molecular Structure
Oxidation-Reduction
Palladium - chemistry
Picolinic Acids - chemistry
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Zusammenfassung:A Cu-catalyzed intramolecular C–H amination for the synthesis of carbazoles has been developed. The key to success is the installation of the picolinamide-based directing group, which is spontaneously removed after the coupling event. The Cu catalysis proceeded smoothly under Pd- and I(III)-free conditions, and its mild oxidation aptitude enables the rapid and concise construction of heteroatom-incorporated carbazole core π-systems.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol501037j