title: Redox-Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine α- and β-C-H Functionalization.
abstract: Cyclic amines such as pyrrolidine and piperidine are known to undergo condensations with aldehydes to furnish pyrrole and pyridine derivatives, respectively. A combined experimental and computational study provides detailed insights into the mechanism of pyrrole formation. A number of reactive intermediates (e.g., azomethine ylides, conjugated azomethine ylides, enamines) were intercepted, outlining strategies for circumventing aromatization as a valuable pathway for amine C-H functionalization.
authors.affiliation: Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey, 08854, USA.
authors.forename: Longle
authors.initials: L
authors.lastname: Ma
authors.affiliation: Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey, 08854, USA.
authors.forename: Anirudra
authors.initials: A
authors.lastname: Paul
authors.affiliation: Department für Chemie, Universität zu Köln, Greinstraße 4, 50939, Köln, Germany.
authors.forename: Martin
authors.initials: M
authors.lastname: Breugst
authors.affiliation: Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey, 08854, USA.
authors.forename: Daniel
authors.initials: D
authors.lastname: Seidel
keywords: C−H functionalization; azomethine ylides; density functional theory; heterocycles; redox-neutral