Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 8, Pages 4037-4043Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00445
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Funding
- Fonds der chemischen Industrie
- DFG [KL 2221/4-2]
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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.
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