Redox‐Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine α‐ and β‐C−H Functionalization. Issue 50 (9th November 2016)

• Record Type: Journal Article
• Authors: Ma, Longle; Paul, Anirudra; Breugst, Martin; Seidel, Daniel
• Is Part Of: Chemistry. Volume 22:Issue 50(2016)
• Page Start: 18179
• Page End: 18189
• Publication Date: 2016-11-09
• Subjects: azomethine ylides -- C−H functionalization -- density functional theory -- heterocycles -- redox-neutral; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201603839
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : Intermediates wanted : A combined experimental and computational study provides detailed insights into the mechanism of pyrrole formation from pyrrolidine and aromatic aldehydes. 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.