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[4+2] or [4+1] Annulation: Changing the Reaction Pathway of a Rhodium‐Catalyzed Process by Tuning the Cp Ligand
57
Citations
41
References
2017
Year
Inorganic ChemistryChemical EngineeringEngineeringConjugated EnynonesRhodium‐catalyzed ProcessNatural SciencesDiversity-oriented SynthesisOrganic ChemistryRhodium‐catalyzed CyclizationOrganometallic CatalysisCatalysisCp LigandChemistryHomogeneous CatalysisHeterocycle ChemistryMolecular CatalysisReaction PathwayBiomolecular Engineering
Abstract A change in reaction pathway was achieved for the first time by tuning the cyclopentadienyl (Cp) ligand used for the rhodium‐catalyzed cyclization of benzamides with conjugated enynones. Depending on the Cp ligand, the reaction pathway switched between [4+2] and [4+1] annulation. Electronic effects turned out to be crucial for the product distribution. The dichotomy was attributed to the alteration of the Lewis acidity of the resultant Cp‐bound rhodium species.
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