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Detection of the Elusive Nitrogen‐Centered Radicals from Catalytic Hofmann–Löffler Reactions
Author(s) -
Bosnidou Alexandra E.,
Duhamel Thomas,
Muñiz Kilian
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201900497
Subject(s) - chemistry , homolysis , amination , catalysis , radical , bond cleavage , bromine , reactivity (psychology) , stoichiometry , medicinal chemistry , electron paramagnetic resonance , halogen , organic chemistry , photochemistry , physics , nuclear magnetic resonance , medicine , alternative medicine , alkyl , pathology
The catalytic Hofmann–Löffler reaction represents a uniquely effective protocol for the formation of pharmaceutically relevant heterocycles and is based on the reactivity of N‐halogenated amines. Herein, we report stoichiometric experimentation toward the detection of a sulfonamidyl radical as the decisive intermediate in this C‐H amination reaction. It can be observed by EPR after homolytic cleavage of the in situ formed N‐halogen bond under the conditions of the iodine or bromine catalyzed Hofmann–Löffler reaction.