Journal
ORGANIC LETTERS
Volume 18, Issue 23, Pages 6128-6131Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b03134
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Funding
- Natural Science Foundation of China (NSFC) [21390400, 21402099]
- Collaborative Innovation Center of Chemical Science and Engineering (Tianjin)
- State Key Laboratory on Elementoorganic Chemistry
- Fundamental Research Funds for the Central Universities [65141002]
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Fluorination mediated by the cyclic hypervalent fluoroiodane reagent (1) often requires an exogenous Lewis acid. The widely accepted Lewis-add-activation model is that a given Lewis acid binds to the oxygen atom of 1 (O-coordination) to polarize the I-O bond. Computational studies of silver-mediated geminal difluorination of styrenes with 1 reveal a new F-coordination model that is energetically much preferred over the commonly accepted O-coordination model. The calculations rationalize the regioselective formation of the geminal difluorination product.
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