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Journal Article

Reaction Mechanism of Iodine-Catalyzed Michael Additions

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Klussmann,  Martin
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

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.


Cite as: https://hdl.handle.net/21.11116/0000-0000-DFAD-3
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.