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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
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Cited 260 time in Scopus
- Authors
- Issue Date
- 2013-08
- Publisher
- American Chemical Society
- Citation
- Journal of the American Chemical Society, Vol.135 No.34, pp.12861-12868
- Abstract
- 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 sp(2) 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.
- ISSN
- 0002-7863
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