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 language | English |
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Pages (from-to) | 6260-6264 |
Number of pages | 5 |
Journal | Organic Letters |
Volume | 20 |
Issue number | 19 |
DOIs | |
State | Published - Oct 5 2018 |