Conjugate Aminocyclization Catalyzed by a Bismuthinidene
Mauro Mato, Feng Wang, Josep Cornellà
Abstract
Abstract We disclose how an N , C , N ‐bismuthinidene is able to promote an intramolecular conjugate amination that affords cyclic carbamates in 91–97% yields. The reaction proceeds at room temperature in short reaction times, requiring a remarkably low loading of a bismuth(I) complex (0.1 mol%) without the need of an additional Brønsted base. Preliminary mechanistic studies suggest that the reaction takes place through a polar pathway involving the conjugate addition of the nucleophilic bismuthinidene, followed by an intramolecular aza‐Michael reaction.
Topics & Concepts
ChemistryConjugateIntramolecular forceAminationCatalysisNucleophileMichael reactionBase (topology)Medicinal chemistryCombinatorial chemistryStereochemistryOrganic chemistryMathematicsMathematical analysisAsymmetric Hydrogenation and CatalysisChemical Synthesis and AnalysisSynthetic Organic Chemistry Methods