Ir(III)-Catalyzed Mild C-H Amidation of Arenes and Alkenes: An Efficient Usage of Acyl Azides as the Nitrogen Source
- Ir(III)-Catalyzed Mild C-H Amidation of Arenes and Alkenes: An Efficient Usage of Acyl Azides as the Nitrogen Source
- 류재윤; 곽재성; 신광민; 이동군; 장석복
- Organic Chemistry; C-H Amidation; Acyl Azide; Ir(III) Catalyst
- Issue Date
- Journal of the American Chemical Society
- VOL 135, NO 34, 12861-12868
- Reported herein is the development of the Ir(III)-catalyzed direct C–H amidation of arenes and alkenes using acyl azides as the nitrogen source. This procedure utilizes an in situ generated cationic half-sandwich iridium complex as a catalyst. The reaction takes place under very mild conditions, and a broad range of sp2 C–H bonds of chelate group-containing arenes and olefins are smoothly amidated with acyl azides without the intervention of the Curtius rearrangement. Significantly, a wide range of reactants of aryl-, aliphatic-, and olefinic acyl azides were all efficiently amidated with high functional group tolerance. Using the developed approach, Z-enamides were readily accessed with a complete control of regio- and stereoselectivity. The developed direct amidation proceeds in the absence of external oxidants and releases molecular nitrogen as a single byproduct, thus offering an environmentally benign process with wide potential applications in organic synthesis and medicinal chemistry.
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