The Journal of Organic Chemistry · 2007 · 152 citations · 22 references
Chemical EngineeringCross-coupling ReactionEngineeringHeterocyclicCatalytic Multicomponent ReactionsOrganic ChemistryOrganometallic CatalysisCatalysisChemistryThree-component Assembly ReactionTransient Azomethine YlideSynthetic ChemistryBiomolecular EngineeringGood Yields
Dirhodium(II) salts efficiently catalyze the three-component assembly reaction of an imine, diazoacetonitrile (DAN), and an activated alkynyl coupling partner to form substituted 1,2-diarylpyrroles in moderate to good yields. The transition-metal-catalyzed decomposition of the diazo compound in the presence of the imine presumably generates a transient azomethine ylide that undergoes cycloaddition with dipolarophiles in a highly convergent manner.
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