Universität zu Köln

Arndt, Thiemo, Wagner, Philip K., Koenig, Jonas J. and Breugst, Martin (2021). Iodine-Catalyzed Diels-Alder Reactions. ChemCatChem, 13 (12). S. 2922 - 2931. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1867-3899

Full text not available from this repository.

Abstract

The Diels-Alder cycloaddition is the most popular pericyclic reaction with numerous applications in synthesis and catalysis. We now demonstrate that we can perform this reaction under mild and metal-free conditions relying on molecular iodine as the catalyst. Cycloadditions with cyclohexadiene, cyclopentadiene, or isoprene with various dienophiles can be performed typically within minutes in moderate to good yields and high endo selectivity. The mechanistic studies including kinetic and DFT investigations clearly indicate a halogen-bond activation and rule out other modes of activation. Furthermore, iodine performs equally well as typical metallic Lewis acids like AlCl3, SnCl4, or TiCl4.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Arndt, Thiemo UNSPECIFIED UNSPECIFIED UNSPECIFIED Wagner, Philip K. UNSPECIFIED UNSPECIFIED UNSPECIFIED Koenig, Jonas J. UNSPECIFIED UNSPECIFIED UNSPECIFIED Breugst, Martin UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-565330
DOI:	10.1002/cctc.202100342
Journal or Publication Title:	ChemCatChem
Volume:	13
Number:	12
Page Range:	S. 2922 - 2931
Date:	2021
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1867-3899
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language ADAPTED PERTURBATION-THEORY; MOLECULAR-IODINE; SILYLIUM ION; BOND DONORS; FREE-ENERGY; BASIS-SETS; ORGANOCATALYSIS; ACID; ACTIVATION; ACCELERATION Multiple languages Chemistry, Physical Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/56533