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  Reaction Mechanism of Iodine-Catalyzed Michael Additions

von der Heiden, D., Bozkus, S., Klussmann, M., & Breugst, M. (2017). Reaction Mechanism of Iodine-Catalyzed Michael Additions. The Journal of Organic Chemistry, 82(8), 4037-4043. doi:10.1021/acs.joc.7b00445.

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 Creators:
von der Heiden, Daniel1, Author
Bozkus, Seyma1, Author
Klussmann, Martin2, Author              
Breugst, Martin1, Author
Affiliations:
1Universität zu Köln, Department für Chemie, Greinstraße 4, 50939 Köln, Germany, ou_persistent22              
2Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445608              

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 Abstract: Molecular iodine, an easy to handle solid, has been successfully employed as a catalyst in different organic transformations 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 Brønsted 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 in the rate-limiting transition state. Our experimental investigations rule out hidden Brønsted acid catalysis by partial decomposition of I2 to HI and suggest a halogen bond activation instead. Finally, molecular iodine turned out to be a similar if not superior catalyst for Michael additions compared with typical Lewis acids.

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Language(s): eng - English
 Dates: 2017-02-242017-03-282017-04-21
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/acs.joc.7b00445
 Degree: -

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Title: The Journal of Organic Chemistry
  Other : J. Org. Chem.
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Chemical Society
Pages: - Volume / Issue: 82 (8) Sequence Number: - Start / End Page: 4037 - 4043 Identifier: ISSN: 0022-3263
CoNE: https://pure.mpg.de/cone/journals/resource/954925416967_1