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Redox-Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine ?- and ?-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.

SUBMITTER: Ma L 

PROVIDER: S-EPMC5193247 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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Redox-Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine α- and β-C-H Functionalization.

Ma Longle L   Paul Anirudra A   Breugst Martin M   Seidel Daniel D  

Chemistry (Weinheim an der Bergstrasse, Germany) 20161109 50

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. ...[more]

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