Universität zu Köln

von der Heiden, Daniel, Bozkus, Seyma, Klussmann, Martin ORCID: 0000-0002-9026-205X and Breugst, Martin ORCID: 0000-0003-0950-8858 (2017). Reaction Mechanism of Iodine-Catalyzed Michael Additions. J. Org. Chem., 82 (8). S. 4037 - 4044. WASHINGTON: AMER CHEMICAL SOC. ISSN 0022-3263

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Abstract

Molecular iodine, an easy to handle solid, has been successfully employed as a catalyst in different organic transformation's for more than 100 years. Despite being active even in very small amounts, the origin of this remarkable catalytic effect is still unknown. Both a halogen bond mechanism as well as hidden Bronsted acid catalysis are frequently discussed as possible explanations. Our kinetic analyses reveal a reaction order of 1 in iodine, indicating that higher iodine species are not involved the rate-limiting transition state. Our experimental investigations rifle out hidden Bronsted acid catalysis by partial deconiposition of I-2 to HI and suggest a halogeri bond activation instead. Finally, molecular iodine turned out to be a similar if not superior,catalyst for Michael additions compared with typical Lewis acids.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code von der Heiden, Daniel UNSPECIFIED UNSPECIFIED UNSPECIFIED Bozkus, Seyma UNSPECIFIED UNSPECIFIED UNSPECIFIED Klussmann, Martin UNSPECIFIED orcid.org/0000-0002-9026-205X UNSPECIFIED Breugst, Martin UNSPECIFIED orcid.org/0000-0003-0950-8858 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-233736
DOI:	10.1021/acs.joc.7b00445
Journal or Publication Title:	J. Org. Chem.
Volume:	82
Number:	8
Page Range:	S. 4037 - 4044
Date:	2017
Publisher:	AMER CHEMICAL SOC
Place of Publication:	WASHINGTON
ISSN:	0022-3263
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 CONJUGATE ADDITION; HALOGEN; INDOLES; ACID; DISPROPORTIONATION; ACTIVATION; ALDEHYDES; CARBONYL; COMPLEX Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/23373