193904-74-4Relevant academic research and scientific papers
Iodine-catalyzed aminosulfonation of hydrocarbons by imidoiodinanes. a synthetic and mechanistic investigation
Lamar, Angus A.,Nicholas, Kenneth M.
, p. 7644 - 7650 (2010)
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).
