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Chemoselective Intramolecular Functionalization of Methyl Groups in Nonconstrained Molecules Promoted by N‑Iodosulfonamides

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journal contribution
posted on 15.05.2015, 00:00 by Nieves R. Paz, Dionisio Rodríguez-Sosa, Haydee Valdés, Ricardo Marticorena, Daniel Melián, M. Belén Copano, Concepción C. González, Antonio J. Herrera
Mechanistic evidence observed in Hofmann–Löffler–Freytag-type reactions has been crucial to achieve the chemoselective functionalization of methyl groups under mild conditions. Radical-mediated methyl iodination and subsequent oxidative deiodination are the key steps in this functionalization, where iodine chemistry has a pivotal role on the formation of the C–N bond. The concepts of single hydrogen atom transfer (SHAT) and multiple hydrogen atom transfer (MHAT) are introduced to describe the observed chemoselectivity.