Beilstein J. Org. Chem.2013,9, 1217–1225, doi:10.3762/bjoc.9.138
aerobic oxygenation of aliphatic C–H bonds with hydroperoxides, which proceeds by 1,5-Hradicalshift of putative oxygen-centered radicals (O-radicals) derived from hydroperoxides followed by trapping of the resulting carbon-centered radicals with molecular oxygen.
Keywords: copper; 1,4-diols; free
radical; 1,5-Hradicalshift; hydroperoxides; molecular oxygen; Introduction
Aliphatic sp3 C–H bonds are ubiquitous components in organic molecules but rather inert towards most of the chemical reactions. It thus remains as one of the most challenging topics in organic synthesis to develop catalytic
oxidative sp3 C–H functionalization with predictable chemo- and regioselectivity [1][2][3][4]. To achieve this goal, we have recently utilized 1,5-H-radicalshift [5][6] with iminyl radical species (N-radicals) generated under Cu-catalyzed aerobic reaction conditions, in which the resulting carbon-centered
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Graphical Abstract
Scheme 1:
Aliphatic C–H oxidation with amidines and ketimines by 1,5-H radical shift.