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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creator	Takamatsu, Kazutaka Hirano, Koji Satoh, Tetsuya Miura, Masahiro
description	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.
doi_str_mv	10.1021/ol501037j
format	Article
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Lett</addtitle><description>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. 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subjects	Amides - chemistry Amination Carbazoles - chemical synthesis Carbazoles - chemistry Copper - chemistry Molecular Structure Oxidation-Reduction Palladium - chemistry Picolinic Acids - chemistry
title	Synthesis of Carbazoles by Copper-Catalyzed Intramolecular C–H/N–H Coupling
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