Nieves R Paz1, Dionisio Rodríguez-Sosa1, Haydee Valdés2, Ricardo Marticorena1, Daniel Melián3, M Belén Copano1, Concepción C González1, Antonio J Herrera1. 1. †Instituto de Productos Naturales y Agrobiología C.S.I.C., Av. Astrofísico Francisco Sánchez 3, 38206 La Laguna, Tenerife, Spain. 2. §Departamento de Física Teórica, Atómica y Óptica, Universidad de Valladolid, Paseo de Belén 7, 47011 Valladolid, Spain. 3. ‡Departamento de Química Orgánica, Universidad de La Laguna, Av. Astrofísico Francisco Sánchez s/n, 38206 La Laguna, Tenerife, Spain.
Abstract
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.
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 n class="Chemical">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.
Authors: Peter Becker; Thomas Duhamel; Christopher J Stein; Markus Reiher; Kilian Muñiz Journal: Angew Chem Int Ed Engl Date: 2017-06-01 Impact factor: 15.336