Journal of the American Chemical Society · 2009 · 251 citations · 14 references
Natural SciencesChemistryCatalysisInorganic ChemistryOrganic ChemistryCatalytic MechanismsHeterocyclic ChemistryMetal CatalysisOrganic SynthesisOxidative AdditionReaction MechanismsCarbonyl Oxygen CoordinationCatalyst Structure - Activity RelationshipsHeterocyclic ReactivityLewis Acid CatalysisLewis AcidityNickel CatalysisOxidative Addition At NickelTransition-metal-catalyzed Heterocycle Synthesis
Regioselective alkenylation and alkylation of 2-pyridone derivatives are achieved through inter- and intramolecular insertion of alkynes, 1,3-dienes, and alkenes into the C(6)-H bond by nickel/AlMe(3) catalysis. Coordination of the heterocycles to the Lewis acid cocatalyst through their basic carbonyl oxygen is considered to be responsible for the regioselective activation of the C-H bonds, probably through oxidative addition to nickel(0).
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New Synthetic Methods to 2-Pyridone Rings
Mercedes Torres, Salvador Gil, Margarita Parra · Current Organic Chemistry · 2005 · 220 citations