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:
CreatorsEmailORCIDORCID Put Code
von der Heiden, DanielUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Bozkus, SeymaUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Klussmann, MartinUNSPECIFIEDorcid.org/0000-0002-9026-205XUNSPECIFIED
Breugst, MartinUNSPECIFIEDorcid.org/0000-0003-0950-8858UNSPECIFIED
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:
KeywordsLanguage
CONJUGATE ADDITION; HALOGEN; INDOLES; ACID; DISPROPORTIONATION; ACTIVATION; ALDEHYDES; CARBONYL; COMPLEXMultiple languages
Chemistry, OrganicMultiple languages
Refereed: Yes
URI: http://kups.ub.uni-koeln.de/id/eprint/23373

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