Publication | Open Access
Palladium-Catalyzed Method for the Synthesis of Carbazoles via Tandem C−H Functionalization and C−N Bond Formation
275
Citations
93
References
2008
Year
Combinatorial ChemistryEngineeringOrganic ChemistryChemistryHeterocycle ChemistryChemical EngineeringMedicinal ChemistryNatural ProductsOrganometallic CatalysisC−n Bond FormationCatalysisSynthesis MethodNew ProtocolEnantioselective SynthesisBiomolecular EngineeringNatural SciencesPalladium-catalyzed MethodBiaryl Amide SubstrateTandem C−h FunctionalizationSynthetic Chemistry
The development of a new method for the assembly of unsymmetrical carbazoles is reported. The strategy involves the selective intramolecular functionalization of an arene C-H bond and the formation of a new arene C-N bond. The substitution pattern of the carbazole product can be controlled by the design of the biaryl amide substrate, and the method is compatible with a variety of functional groups. The utility of the new protocol was demonstrated by the concise synthesis of three natural products from commercially available materials.
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