Carboxylate-Assisted Iridium-Catalyzed C-H Amination of Arenes with Biologically Relevant Alkyl Azides

Tao Zhang, Xuejiao Hu, Zhen Wang, Tiantian Yang, Hao Sun, Guigen Li, Hongjian Lu

Research output: Contribution to journalArticle

32 Scopus citations

Abstract

An iridium-catalyzed C-H amination of arenes with a wide substrate scope is reported. Benzamides with electron-donating and -withdrawing groups and linear, branched, and cyclic alkyl azides are all applicable. Cesium carboxylate is crucial for both reactivity and regioselectivity of the reactions. Many biologically relevant molecules, such as amino acid, peptide, steroid, sugar, and thymidine derivatives can be introduced to arenes with high yields and 100 % chiral retention. Ir responsible! A direct C-H amination between benzamide derivatives and various alkyl azides was achieved using iridium catalysis (see scheme; NTf=trifluoromethanesulfonyl amide). Cesium carboxylate was found to be the promoter and regiocontroller of this reaction. By this method, many biological active molecules can be introduced to benzamide components with high yields and 100 % chiral retention.

Original languageEnglish
Pages (from-to)2920-2924
Number of pages5
JournalChemistry - A European Journal
Volume22
Issue number9
DOIs
StatePublished - Feb 24 2016

Keywords

  • C-H activation
  • amides
  • azides
  • homogeneous catalysis
  • iridium

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