Universität zu Köln

Ma, Longle ORCID: 0000-0002-6359-4702, Paul, Anirudra, Breugst, Martin ORCID: 0000-0003-0950-8858 and Seidel, Daniel ORCID: 0000-0001-6725-111X (2016). Redox-Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine alpha- and beta-C-H Functionalization. Chem.-Eur. J., 22 (50). S. 18179 - 18190. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3765

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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.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Ma, Longle UNSPECIFIED orcid.org/0000-0002-6359-4702 UNSPECIFIED Paul, Anirudra UNSPECIFIED UNSPECIFIED UNSPECIFIED Breugst, Martin UNSPECIFIED orcid.org/0000-0003-0950-8858 UNSPECIFIED Seidel, Daniel UNSPECIFIED orcid.org/0000-0001-6725-111X UNSPECIFIED
URN:	urn:nbn:de:hbz:38-252606
DOI:	10.1002/chem.201603839
Journal or Publication Title:	Chem.-Eur. J.
Volume:	22
Number:	50
Page Range:	S. 18179 - 18190
Date:	2016
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1521-3765
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language BOND FUNCTIONALIZATION; ASYMMETRIC-SYNTHESIS; TERMINAL ALKYNES; SECONDARY-AMINES; HYDRIDE TRANSFER; CYCLOADDITION REACTIONS; CONDENSATION REACTIONS; PHOTOREDOX CATALYSIS; UNSATURATED AMINES; AZOMETHINE YLIDES Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/25260