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Using phenyl iodide as catalyst in the presence of pyr⋅9 HF as fluorine source, product 2 a was formed in 12 % yield (Table 1, entry 1) with full consumption of starting material 1 a. 11f Wang and co-workers 11i presented a study on electrophilic fluorination of styryl boronate derivatives (Figure 1 e) affording geminal difluorinated products. In this process the electrophilic fluorination by hypervalent iodines proceeds through a carbocation intermediate, which undergoes migration of an alkyl or aryl group. Recently, the Jacobsen group 11f reported an asymmetric 1,3-difluorinative Wagner–Meerwein rearrangement of β-substituted styrene derivatives (Figure 1 d). Previous studies have shown 11 that fluorination of styrene derivatives with hypervalent iodines usually proceeds via rearrangement involving cationic phenonium ion intermediates (Figure 1 c). In particular, fluorination of alkenes with hypervalent iodines proceed via these intermediates. 10 Electrophilic fluorination reactions are also known to proceed via carbocations or electron-deficient carbon centers. Interestingly, this B-N hemilability lends a migration aptitude to Bmida group, which is in the same magnitude as the ability of H/alkyl/aryl groups to undergo migration to electron deficient carbon centers. Mechanistic studies by Yudin and co-workers 9 revealed that the high migration aptitude of MIDA boronate in this process is due to the hemilabile bonding of nitrogen to boron in the Bmida group. In this reaction the MIDA boronate group undergoes a migration process, which is very similar to the H/alkyl migration to electron deficient carbon centers. 5 The groups of Yudin 6 and Burke 7 reported interesting Meinwald-type rearrangements 8 of oxiranyl MIDA boronates (Figure 1 b). The most common is migration of alkyl/aryl groups and hydrogen between two vicinal carbon atoms (Figure 1 a). The Wagner–Meerwein rearrangement is obviously one of the most important and most studied processes in organic chemistry. 3 Here, we present an electrophilic fluorination reaction of vinyl boronate reagents proceeding via MIDA boronate 4 rearrangement. 2 In a particularly interesting class of reagents the boron containing groups control the outcome of the fluorination reaction. 1 Organoboron reagents are very attractive in synthesis of organofluorine compounds, which are employed in many fields of life-sciences, such as in pharmaceutical, agrochemical and medical diagnostic areas. Synthetic boron and fluorine chemistries have received a lot of attention recently.