Iron-catalyzed intramolecular C-H amination for the synthesis of N-H carbazoles and indoles

The development of aerobic oxidative C-H/N-H cross-coupling catalyzed by the first-row transition metals is attractive yet challenging. Here, the first iron-catalyzed intramolecular cross-dehydrogenative coupling for the synthesis of carbazoles and indoles using air as the oxidant is reported. The g...

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Veröffentlicht in:Green chemistry : an international journal and green chemistry resource : GC 2023-06, Vol.25 (11), p.4463-4468
Hauptverfasser: Wang, Zheng-Lin, Zhang, Yun-Hao, Huang, Jun-Yu, Zhou, Jian, Yu, Ya-Qin, Feng, Dexin, Xu, Da-Zhen
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Sprache:eng
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Zusammenfassung:The development of aerobic oxidative C-H/N-H cross-coupling catalyzed by the first-row transition metals is attractive yet challenging. Here, the first iron-catalyzed intramolecular cross-dehydrogenative coupling for the synthesis of carbazoles and indoles using air as the oxidant is reported. The general and efficient protocol allows for C-N bond formation under green conditions with excellent functional group compatibility, delivering a wide range of N-H carbazoles and indoles in good yields. Impressively, all carbazoles are prepared from 2-cyclohexenyl aminoarenes with the loss of 6Hs via a C-H amination and aromatization process. Furthermore, it also works for C-O bond formation. An iron-catalyzed intramolecular dehydrogenative coupling for the synthesis of N-H carbazoles and indoles with excellent functional group tolerance using air as the terminal oxidant is reported.
ISSN:1463-9262
1463-9270
DOI:10.1039/d3gc00518f