ja0c00868_si_001.pdf (15.79 MB)
Tuning Triplet Energy Transfer of Hydroxamates as the Nitrene Precursor for Intramolecular C(sp3)–H Amidation
journal contribution
posted on 2020-03-16, 13:35 authored by Hoimin Jung, Hyeyun Keum, Jeonguk Kweon, Sukbok ChangReported herein is the design of
a photosensitization strategy
to generate triplet nitrenes and its applicability for the intramolecular
C–H amidation reactions. Substrate optimization by tuning physical
organic parameters according to the proposed energy transfer pathway
led us to identify hydroxamates as a convenient nitrene precursor.
While more classical nitrene sources, representatively organic azides,
were ineffective under the current photosensitization conditions,
hydroxamates, which are readily available from alcohols or carboxylic
acids, are highly efficient in accessing synthetically valuable 2-oxazolidinones
and γ-lactams by visible light. Mechanism studies supported
our working hypothesis that the energy transfer path is mainly operative.
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2- oxazolidinonesphotosensitization strategytriplet nitrenescarboxylic acidsNitrene PrecursorTuning Triplet Energy Transferenergy transfer pathenergy transfer pathwayphotosensitization conditionsγ- lactamsnitrene precursorhydroxamateaccessing syntheticallynitrene sourcesSubstrate optimizationMechanism studies
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