Hydrofluoroether Synthesis through One-Pot Anodic Iodoalkoxylation of Alkenes
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Date
2024
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Abstract
The incorporation of carbon-fluorine bonds can profoundly influence the chemical and physical properties of drugs, agrochemicals, and materials. Different methods allow the installation of CF3, CF2H units and C-F bonds including trifluoro- and difluoromethoxylations, reflecting the limited diversity of reactions available to synthetic chemists. We introduce the 2,2,2-trifluoroethoxy group through an electro-oxidative iodination of alkenes as a versatile substituent for fluorine chemists. An iodoarene serves as an unusual iodine source facilitating the 1,2-iodoalkoxylation of a broad range of industrially relevant aliphatic alkenes in high yields (31-98%) showing high Markovnikov regioselectivity.
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Keywords
Electrochemistry, Hydrofluoroethers, Hypervalent iodine, Iodination, 2,2,2-trifluoroethoxy