Copper-mediated C(sp(3))-H azidation with Me3SiN3: synthesis of imidazoles from ketones and aldehydes

Copper-mediated C(sp(3))-H azidation with Me3SiN3: synthesis of imidazoles from ketones and aldehydes

The efficient construction of 2,4,5-trisubstituted imidazoles, through a copper-mediated three-component reaction involving ketones, aldehydes, and Me3SiN3, has been developed. During the process, 4 C-N bonds were formed sequentially. Experimental results and DFT calculations suggested that azidatio...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2016-05, Vol.52 (38), p.6467-6470
Hauptverfasser: Xie, Zeqiang, Deng, Jiaojiao, Qiu, Zhiping, Li, Juan, Zhu, Qiang
Format: Artikel
Sprache:eng
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Zusammenfassung:The efficient construction of 2,4,5-trisubstituted imidazoles, through a copper-mediated three-component reaction involving ketones, aldehydes, and Me3SiN3, has been developed. During the process, 4 C-N bonds were formed sequentially. Experimental results and DFT calculations suggested that azidation of the alpha methylene group of the ketone was the key C-N bond-forming step.
ISSN:1364-548X
DOI:10.1039/c6cc01863g