Multiple Halogenation of Aliphatic C-H Bonds within the Hofmann-Loffler Manifold

DEL CASTILLO, ESTEFANÍA; MARTÍNEZ, MARIO D.; BOSNIDOU, ALEXANDRA E.; DUHAMEL, THOMAS; O'BROIN, CALVIN Q.; ZHANG, HONGWEI; ESCUDERO-ADÁN, EDUARDO C.; MARTÍNEZ-BELMONTE, MARTA; MUÑIZ, KILIAN

CHEMISTRY-A EUROPEAN JOURNAL

WILEY-V C H VERLAG GMBH

Año: 2018

0947-6539

An innovative approach to position-selective polyhalogenation of aliphatic hydrocarbon bonds is presented. The reaction proceeded within the Hofmann-Löffler manifold with amidyl radicals as the sole mediators to induce selective 1,5- and 1,6-hydrogen-atom transfer followed by halogenation. Multiple halogenation events of up to four innate C−H bond functionalizations were accomplished. The broad applicability of this new entry into polyhalogenation and the resulting synthetic possibilities were demonstrated for a total of 27 different examples including mixed halogenations.