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Iodine-Catalyzed Aminosulfonation of Hydrocarbons by Imidoiodinanes. a Synthetic and Mechanistic Investigation

  作者 LAMAR ANGUS A; NICHOLAS KENNETH M  
  选自 期刊  Journal of Organic Chemistry;  卷期  2010年75-22;  页码  7644-7650  
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[摘要]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 I-2 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),I-y (x = 1, y = 2, or x = 3, y = 4)

 
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