title: NHC-catalyzed intramolecular redox amidation for the synthesis of functionalized lactams.
abstract: A very efficient NHC-catalyzed lactamization reaction is reported. For most cases, the ring expansion reaction proceeds to cleanly furnish five- and six-membered N-Ts and N-Bn lactams, without the need for further purification. Evidence is presented suggesting a dual role for the stoichiometric base: (1) deprotonation of the triazolium precatalyst and (2) activation of the nitrogen leaving group through hydrogen bonding.
authors.affiliation: Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK S7N 5C9, Canada.
authors.forename: Karen
authors.initials: K
authors.lastname: Thai
authors.forename: Li
authors.initials: L
authors.lastname: Wang
authors.forename: Travis
authors.initials: T
authors.lastname: Dudding
authors.forename: François
authors.initials: F
authors.lastname: Bilodeau
authors.forename: Michel
authors.initials: M
authors.lastname: Gravel
mesh_terms: D000586:Amination; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D006571:Heterocyclic Compounds; D007769:Lactams; C030011:carbene; D006859:Hydrogen; D008697:Methane