Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 14, Pages 5279-5282Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja501879c
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Funding
- Bristol-Myers Squibb
- NSS (PhD) A*STAR
- G. E. Hewitt Foundation
- AvH Foundation
- NIH/NIGMS [GM-106210]
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A simple method for direct C-H imidation is reported using a new perester-based self-immolating reagent and a base-metal catalyst. The succinimide products obtained can be easily deprotected in situ (if desired) to reveal the corresponding anilines directly. The scope of the reaction is broad, the conditions are extremely mild, and the reaction is tolerant of oxidizable and acidlabile functionality, multiple heteroatoms, and aryl iodides. Mechanistic studies indicate that ferrocene (Cp2Fe) plays the role of an electron shuttle in the decomposition of the perester reagent, delivering a succinimidyl radical ready to add to an aromatic system.
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