Journal of the American Chemical Society · 2006 · 646 citations · 7 references
Natural SciencesChemistryCatalysisOrganic ChemistryOrganometallic ChemistryCatalyst DesignCatalyst PreparationCatalyst SynthesisCatalytic MechanismsDiversity-oriented SynthesisOrganic SynthesisArylation ReactionsCatalyst Development For SynthesisIndole ChemistryIndole DerivativesIndole SynthesisMild Reaction ConditionsPalladium Catalysts
This communication describes the rational development of a PdII-catalyzed method for the direct 2-arylation of indoles using [Ar-IIII-Ar]BF4. These reactions proceed under remarkably mild conditions (often at room temperature and in the presence of ambient air and moisture), and these features are believed to be the result of a PdII/IV mechanism operating in these systems. These transformations can be used to prepare functionally diverse 2-arylated indoles and pyrroles, and their potential utility has been expanded by the development of an in situ procedure for generating the iodine(III) arylating reagents.
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