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Multiple Halogenation of Aliphatic C−H Bonds within the Hofmann–Löffler Manifold
Author(s) -
Del Castillo Estefanía,
Martínez Mario D.,
Bosnidou Alexandra E.,
Duhamel Thomas,
O'Broin Calvin Q.,
Zhang Hongwei,
EscuderoAdán Eduardo C.,
MartínezBelmonte Marta,
Muñiz Kilian
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804504
Subject(s) - halogenation , chemistry , radical , manifold (fluid mechanics) , hydrogen atom , hydrogen bond , hydrocarbon , medicinal chemistry , organic chemistry , group (periodic table) , molecule , engineering , mechanical engineering
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.