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ChemInform Abstract: Iodine-Catalyzed Aminosulfonation of Hydrocarbons by Imidoiodinanes. A Synthetic and Mechanistic Investigation
- Source :
- ChemInform. 42
- Publication Year :
- 2011
- Publisher :
- Wiley, 2011.
-
Abstract
- The amino-functionalization of a range of benzylic and some aliphatic saturated and unsaturated hydrocarbons by reaction with imido-iodinanes (PhI═NSO2Ar) is catalyzed by I2 under operationally simple and mild conditions. The first examples of 1,2-functionalization of unactivated C−H bonds using imido-iodinanes as aminating agents are reported. Mechanistic investigations, including Hammett analysis, kinetic isotope effects, a cyclopropane clock experiment, and stereoselectivity tests, are indicative of a stepwise pathway in C−N bond formation. Investigation into the nature of the active aminating species has led to the isolation of a novel aminating agent formulated as (ArSO2N)xIy (x = 1, y = 2; or x = 3, y = 4).
Details
- ISSN :
- 09317597
- Volume :
- 42
- Database :
- OpenAIRE
- Journal :
- ChemInform
- Accession number :
- edsair.doi...........d40f4dc3736842196660d8e694a4dce9