Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 40, Pages 6361-6365Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201900497
Keywords
Amines; Radicals; Amination; EPR spectroscopy; Pyrrolidines
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The catalytic Hofmann-Loffler 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-Loffler reaction.
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