Hypervalent iodine mediated alkene fluorination Alastair Lennox University of Bristol, UK
The incorporation of fluorine into bioactive molecules is a well-established technique for improving metabolic stability, biocompatibility and potency, which are all essential for the discovery of new lifesaving pharmaceuticals and selective agrochemicals. Thus, the continual development of new reactions that are more selective, sustainable and scalable is of high importance. A few years ago, we established a research programme into the use of electrochemically generated, hypervalent iodine mediators that are suitable for the selective fluorination of alkenes. By exploiting the innate reactivity of the fluoride anion and combining it with electrochemical anodic oxidation, inexpensive and sustainable processes can be realised. The physical separation of the oxidation and reduction reactions in electrochemistry, allows for a selective oxidation on the anode and a milder and waste-free oxidant to be reduced on the cathode. We have thus far reported this strategy for the difluorination [1] and intramolecular arylfluorination [2] of readily-available, unactivated alkenes. In this presentation, I will briefly describe these reactions and their features, but I will spend most of the time describing our more recent, unpublished, results on the development of hyper valent iodine mediated alkene fluorination reactions. Such reactions include various fluorofunctionalisations of alkenes. The control of regio, chemo and diastereoselectivity will be discussed, as will the proposed mechanisms of action and selectivity control. References 1. Doobary, S., Poole, D. L., Lennox, A. J. J., J. Org. Chem. 2021 , 86 , 16095–16103. 2. Doobary, S., Sedikides, A. T.; Caldora, H. P.; Poole, D. L.; Lennox, A. J. J.; Angew. Chem. Int. Ed. 2020 , 59 , 1155–1160.
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