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Title

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

AuthorsPaz, Nieves R.; Rodríguez Sosa, Dionisio ; Valdés, Haydée; Marticorena, Ricardo; Melián, Daniel; Copano, Belén; González Martín, Concepción C. ; Herrera, Antonio J.
Issue Date1-May-2015
PublisherAmerican Chemical Society
CitationOrganic Letters 17(10): 2370-2373 (2015)
AbstractMechanistic 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.
Publisher version (URL)https://doi.org/10.1021/acs.orglett.5b00866
URIhttp://hdl.handle.net/10261/181030
Identifiersdoi: 10.1021/acs.orglett.5b00866
issn: 1523-7060
e-issn: 1523-7052
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