European Journal of Organic Chemistry · 2013 · 44 citations · 21 references
Natural SciencesChemistryBioorganic ChemistryCatalysisOrganic ChemistryCatalyst PreparationCatalytic MechanismsCross-coupling ReactionsOrganic SynthesisIndole ChemistryIndole DerivativesIndole SynthesisNickel-catalyzed Cross-couplingOxidative CouplingOxidative Coupling ReactionsOxidative Cross-coupling
Abstract The n Bu 4 NI‐catalyzed intramolecular cross‐dehydrogenative coupling (CDC) reaction has been applied to the synthesis of 1 H ‐indole derivatives. Intramolecular oxidative coupling of N ‐arylenamines proceeded in the presence of a catalytic amount of n Bu 4 NI and tert ‐butyl hydroperoxide (TBHP) to afford the corresponding 1 H ‐indole derivatives in good‐to‐excellent yields. A preliminary study of the synthesis of 3 H ‐indole is also reported. This is a rare example of the n Bu 4 NI‐catalyzed C–C bond‐forming CDC reaction.
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Alison N. Campbell, Shannon S. Stahl · Accounts of Chemical Research · 2012 · 788 citations · Full text