Iridium-Catalyzed Unreactive C(sp3)-H Amination with 2,2,2-Trichloroethoxycarbonyl Azide

Tao Zhang, Xuejiao Hu, Xunqing Dong, Guigen Li, Hongjian Lu

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

An additive-assisted iridium-catalyzed directed C(sp3)-H amination with 2,2,2-trichloroethoxycarbonyl azide as an amino source is reported. Both carboxylate anions and the corresponding cations in the additives are crucial to achieve satisfactory efficiency. Sodium acetate or n-pentanoic acid can promote the amination of various primary C(sp3)-H bonds adjacent to secondary, tertiary, and quaternary carbons in ketoximes or N-aromatic heterocycles, respectively, providing a practical route to versatile β-amino ketoxime and N-heteroaryl ethanamine derivatives. The amination products can be treated as isocyanate analogues and can be converted to other useful amino functionalities. An iridacyclic compound was isolated and identified as a plausible intermediate.

Original languageEnglish
Pages (from-to)6260-6264
Number of pages5
JournalOrganic Letters
Volume20
Issue number19
DOIs
StatePublished - Oct 5 2018

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