Universität zu Köln

Koenig, Jonas J., Arndt, Thiemo, Gildemeister, Nora, Neudoerfl, Joerg-M. and Breugst, Martin ORCID: 0000-0003-0950-8858 (2019). Iodine-Catalyzed Nazarov Cyclizations. J. Org. Chem., 84 (12). S. 7587 - 7606. WASHINGTON: AMER CHEMICAL SOC. ISSN 1520-6904

Full text not available from this repository.

Abstract

The Nazarov cyclization is an important pericyclic reaction that allows the synthesis of substituted cyclopentenones. We now demonstrate that this reaction can be performed under very mild, metal-free reaction conditions using molecular iodine as the catalyst. A variety of different divinyl ketones including aromatic systems undergo the iodine-catalyzed reaction with moderate to very good yields in both polar and apolar solvents. Our mechanistic studies indicate that the Nazarov system is activated through a halogen bond between the carbonyl group and the catalyst, and other modes of action like Bronsted acid or iodonium ion catalysis are unlikely. Furthermore, addition of iodine to the double bond or a putative iodine-catalyzed cis-trans isomerization of the employed olefins seem not to be an important side reaction here.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Koenig, Jonas J. UNSPECIFIED UNSPECIFIED UNSPECIFIED Arndt, Thiemo UNSPECIFIED UNSPECIFIED UNSPECIFIED Gildemeister, Nora UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Breugst, Martin UNSPECIFIED orcid.org/0000-0003-0950-8858 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-137512
DOI:	10.1021/acs.joc.9b01083
Journal or Publication Title:	J. Org. Chem.
Volume:	84
Number:	12
Page Range:	S. 7587 - 7606
Date:	2019
Publisher:	AMER CHEMICAL SOC
Place of Publication:	WASHINGTON
ISSN:	1520-6904
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 NONCOVALENT INTERACTIONS; DENSITY FUNCTIONALS; EFFICIENT CATALYSIS; ORGANIC-SYNTHESIS; MOLECULAR-IODINE; SOLID-STATE; BASIS-SETS; HALOGEN; BOND; ACTIVATION Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/13751