Organic Letters · 2012 · 83 citations · 48 references
Natural SciencesChemistryMedicinal ChemistryBioorganic ChemistryOrganic ChemistrySynthetic Medicinal ChemistryCross-coupling ReactionsHeterocycle SynthesisRadical ReactionsOxidationOxidation-reduction ConditionsOxidative CouplingOxidative Cross-couplingRadical Mediated C - H FunctionalizationTransition Metal-catalyzed SynthesisTransition-metal-catalyzed Functionalization
An intramolecular-dehydrogenative-coupling (IDC) using "transition-metal-free" oxidation conditions has been achieved to synthesize a variety of 2-oxindoles bearing an all-carbon quaternary stereogenic center at the benzylic position. The methodology involves a one-pot C-alkylation of β-N-arylamido esters (3, 6) with alkyl halides using potassium tert-butoxide concomitant with a dehydrogenative coupling. A radical-mediated pathway has been tentatively proposed for the oxidative process.
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