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Direct Oxidative C–H Arylation of Benzoxazoles with Arylsulfonyl Hydrazides Promoted by Palladium Complexes
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2012
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Chemical EngineeringCross-coupling ReactionEngineeringPalladium ComplexesNatural SciencesDiversity-oriented SynthesisAryl SourcesOrganic ChemistryHalogen SubstituentsOrganometallic CatalysisCatalysisChemistryArylsulfonyl HydrazidesArylsulfonyl Hydrazides Promoted
This study describes a direct oxidative C-2 arylation of benzoxazoles using arylsulfonyl hydrazides as the aryl sources. A simple catalyst system [Pd(OAc)<sub>2</sub> and Ph<sub>3</sub>P] allows the reactions to proceed smoothly under oxidative reaction conditions. Other heteroarenes such as caffeine and benzothiazole are also applicable substrates. Notably, this catalytic system tolerates halogen substituents which provides a useful complement to the current cross-coupling reactions which use aryl halides.